Merge pull request 'fix(about): About Outpost opens Settings' About section, no popup window' (#10) from fix/about-menu-no-popup into main

Reviewed-on: #10

.gitea/issue_template/bug_report.yaml

@@ -0,0 +1,43 @@
+name: Bug Report
+about: Report a bug in Outpost
+labels:
+  - "type: bug"
+body:
+  - type: markdown
+    attributes:
+      value: |
+        Outpost is early alpha — please check the version in About (or your build's commit) is current before filing, and mention which platform (macOS only, for now) and OS version you're on.
+  - type: input
+    id: summary
+    attributes:
+      label: Summary
+      placeholder: Brief description of the bug
+    validations:
+      required: true
+  - type: textarea
+    id: steps
+    attributes:
+      label: Steps to Reproduce
+      value: |
+        1.
+        2.
+        3.
+    validations:
+      required: true
+  - type: textarea
+    id: expected
+    attributes:
+      label: Expected Behavior
+    validations:
+      required: true
+  - type: textarea
+    id: actual
+    attributes:
+      label: Actual Behavior
+    validations:
+      required: true
+  - type: textarea
+    id: context
+    attributes:
+      label: Additional Context
+      description: Logs, screenshots, macOS version, Outline server version, etc.

.gitea/issue_template/config.yml

@@ -0,0 +1 @@
+blank_issues_enabled: false

.gitea/issue_template/documentation.yaml

@@ -0,0 +1,30 @@
+name: Documentation
+about: Report missing, incorrect, or outdated documentation
+labels:
+  - "type: docs"
+body:
+  - type: input
+    id: page
+    attributes:
+      label: Affected Page / File
+      placeholder: "e.g. SETUP.md, docs/ARCHITECTURE.md, CLAUDE.md"
+    validations:
+      required: true
+  - type: dropdown
+    id: type
+    attributes:
+      label: Type
+      options:
+        - Missing documentation
+        - Incorrect / outdated information
+        - Unclear or confusing
+        - Typo / formatting
+    validations:
+      required: true
+  - type: textarea
+    id: description
+    attributes:
+      label: Description
+      description: What needs to change and why?
+    validations:
+      required: true

.gitea/issue_template/feature_request.yaml

@@ -0,0 +1,38 @@
+name: Feature Request
+about: Suggest something for Outpost
+labels:
+  - "type: feature"
+body:
+  - type: markdown
+    attributes:
+      value: |
+        Outpost is early alpha and tracking Outline's own web app for parity (see [`CLAUDE.md`](../../CLAUDE.md) for the phased build order) — a request that's "just do what web Outline does" is easier to act on than a net-new idea.
+  - type: input
+    id: summary
+    attributes:
+      label: Summary
+      placeholder: What do you want Outpost to do?
+    validations:
+      required: true
+  - type: textarea
+    id: motivation
+    attributes:
+      label: Motivation
+      description: What's the use case? What can't you do today without this?
+    validations:
+      required: true
+  - type: textarea
+    id: proposal
+    attributes:
+      label: Proposed Behavior
+      description: How should it work? Point at how Outline's web app does it, if relevant.
+  - type: dropdown
+    id: platform
+    attributes:
+      label: Platform
+      options:
+        - macOS
+        - iOS / iPadOS
+        - Both / platform-agnostic
+    validations:
+      required: true

.gitea/issue_template/question.yaml

@@ -0,0 +1,20 @@
+name: Question
+about: Ask something about setup, usage, or how Outpost works
+labels:
+  - "type: question"
+body:
+  - type: markdown
+    attributes:
+      value: |
+        Check [`SETUP.md`](../../SETUP.md) first — most "how do I get this running" questions are answered there.
+  - type: textarea
+    id: question
+    attributes:
+      label: Question
+    validations:
+      required: true
+  - type: textarea
+    id: context
+    attributes:
+      label: Context
+      description: What are you trying to do? Anything you've already tried?

.gitea/issue_template/security_vulnerability.yaml

@@ -0,0 +1,46 @@
+name: Security Vulnerability
+about: Report a security vulnerability in this repository
+labels:
+  - "type: security"
+  - "priority: critical"
+body:
+  - type: markdown
+    attributes:
+      value: |
+        **Please do not disclose sensitive details publicly.** If this is a critical vulnerability,
+        email security@psmattas.com directly instead of filing this issue — see [`SECURITY.md`](../../SECURITY.md).
+  - type: input
+    id: summary
+    attributes:
+      label: Summary
+      placeholder: Brief description of the vulnerability
+    validations:
+      required: true
+  - type: dropdown
+    id: severity
+    attributes:
+      label: Severity
+      options:
+        - Critical — active exploit / data exposure
+        - High — exploitable with moderate effort
+        - Medium — limited impact or requires specific conditions
+        - Low — informational / hardening suggestion
+    validations:
+      required: true
+  - type: textarea
+    id: description
+    attributes:
+      label: Description
+      description: What is the vulnerability and how can it be exploited?
+    validations:
+      required: true
+  - type: textarea
+    id: reproduction
+    attributes:
+      label: Steps to Reproduce
+      description: Provide enough detail for someone to verify the issue.
+  - type: textarea
+    id: remediation
+    attributes:
+      label: Suggested Remediation
+      description: If you have a fix in mind, describe it here.

.gitea/pull_request_template.yml

@@ -0,0 +1,38 @@
+name: Pull Request
+about: Standard pull request template
+body:
+  - type: input
+    id: ticket
+    attributes:
+      label: Related Issue
+      description: "Leave blank if there isn't one."
+      placeholder: "Resolves #"
+
+  - type: textarea
+    id: summary
+    attributes:
+      label: Summary
+      description: "One or two sentences — what and why."
+    validations:
+      required: true
+
+  - type: textarea
+    id: changes
+    attributes:
+      label: Changes
+      value: "-\n-"
+    validations:
+      required: true
+
+  - type: checkboxes
+    id: checklist
+    attributes:
+      label: Checklist
+      options:
+        - label: Self-reviewed
+          required: true
+        - label: "`OutlineKit` tests added/updated and passing (`swift test`), if this touches the REST layer"
+          required: false
+        - label: Verified in Xcode (there's no reliable CLI build for the app target)
+          required: true
+        - label: Docs updated (if applicable)

.gitignore

@@ -60,3 +60,9 @@ fastlane/report.xml
 fastlane/Preview.html
 fastlane/screenshots/**/*.png
 fastlane/test_output
+
+# scripts/package-dmg.sh output
+/dist/
+
+# Local working checklist - intentionally never version controlled
+/TODO.local.md

CODEOWNERS

@@ -0,0 +1,37 @@
+# Outpost Code Owners
+# These users are automatically requested for review on PRs.
+# Format: path @username
+#
+# Rules are evaluated in order, last match wins — so the specific paths
+# below stay pinned to @psmattas even if `*` is ever opened up to other
+# contributors/reviewers as the project grows. These are the
+# supply-chain, governance, and CI-relevant files where an accidental or
+# malicious change has outsized blast radius for a public repo.
+
+* @psmattas
+
+# Repo governance / legal — changes here affect every contributor.
+/LICENSE @psmattas
+/CODEOWNERS @psmattas
+/CONTRIBUTING.md @psmattas
+/SECURITY.md @psmattas
+/SETUP.md @psmattas
+
+# CI, issue/PR automation, review requirements — tampering here can
+# bypass the protections this very file is trying to set up.
+/.gitea/ @psmattas
+
+# Dependency supply chain — a swapped or re-pinned package here can pull
+# in arbitrary code at build time.
+/OutlineKit/Package.swift @psmattas
+/OutlineKit/Package.resolved @psmattas
+/Outpost.xcodeproj/project.xcworkspace/xcshareddata/swiftpm/Package.resolved @psmattas
+
+# Build/signing/versioning config and release tooling.
+/Outpost.xcodeproj/project.pbxproj @psmattas
+/scripts/ @psmattas
+
+# Project direction — architecture/scope decisions shouldn't drift via a
+# drive-by PR.
+/CLAUDE.md @psmattas
+/docs/ARCHITECTURE.md @psmattas

CONTRIBUTING.md

@@ -0,0 +1,71 @@
+# Contributing to Outpost
+
+Thank you for contributing. Please read this guide before opening issues or PRs.
+
+Outpost is early alpha (`0.0.x`) — expect the codebase and conventions here to shift as Phase 1 (see [`docs/ARCHITECTURE.md`](docs/ARCHITECTURE.md)) settles. If something in this guide is stale, flag it.
+
+---
+
+## Branching
+
+Branch from `main` using `type/short-description`:
+
+```bash
+git checkout -b feature/document-permissions
+git checkout -b fix/sidebar-context-menu
+```
+
+---
+
+## Commit Messages
+
+Follow the Conventional Commits standard: `type(scope): message`.
+
+| Type | Description |
+| :--- | :--- |
+| `feat` | New feature |
+| `fix` | Bug fix |
+| `docs` | Documentation |
+| `style` | Formatting |
+| `refactor` | Refactor |
+| `perf` | Performance |
+| `test` | Tests |
+| `build` | Build system |
+| `ci` | CI/CD config |
+| `chore` | Maintenance |
+
+**Examples:**
+- `feat(collections): add document right-click context menu`
+- `fix(reader): correct off-main AppKit calls in save action`
+
+---
+
+## Pull Requests
+
+- Link the related issue in your PR description, if any
+- Keep PRs focused — one feature or fix per PR
+- Self-review before requesting review
+- Run the tests that apply to what you touched (see below) and confirm the app still launches and behaves correctly in Xcode
+
+### Testing
+
+- **`OutlineKit`** (the REST client package) has real unit test coverage:
+  ```bash
+  cd OutlineKit && swift test
+  ```
+- **The `Outpost` app target** has no meaningful CLI build path — `xcodebuild` from the command line is not a reliable way to verify it in this project's current setup. Build and run through Xcode, and manually verify the feature you changed (and anything obviously adjacent) before opening a PR.
+
+---
+
+## Labels
+
+Issues and PRs use two label prefixes:
+
+- `type:` — what kind of change/issue this is (`type: bug`, `type: docs`, `type: security`, ...)
+- `priority:` — how urgent it is (used mainly for security reports)
+
+---
+
+## Questions
+
+Open an issue — this is a single-repo project, there's no separate issue tracker to route to.

OutlineKit/Sources/OutlineKit/Caching/CachedPayload.swift

@@ -0,0 +1,18 @@
+import Foundation
+import SwiftData
+
+/// Generic key/value row backing `OfflineCacheStore` — one table for every
+/// cached response shape instead of a `@Model` per Outline type, so adding a
+/// new cached endpoint never needs a schema migration.
+@Model
+public final class CachedPayload {
+    @Attribute(.unique) public var key: String
+    public var payload: Data
+    public var cachedAt: Date
+
+    public init(key: String, payload: Data, cachedAt: Date) {
+        self.key = key
+        self.payload = payload
+        self.cachedAt = cachedAt
+    }
+}

OutlineKit/Sources/OutlineKit/Caching/CachingOutlineAPIClient.swift

@@ -0,0 +1,721 @@
+import Foundation
+
+/// Decorates `LiveOutlineAPIClient` (or any `OutlineAPIClient`) with offline
+/// support at the existing protocol boundary, so no view model needs to know
+/// the network exists:
+///
+/// - **Reads** (`documentInfo`, `listDocuments`, `documentsList`,
+///   `listViewedDocuments`, `listCollections`, `collectionInfo`): read-through
+///   cache. Always tries live first — never pre-checks reachability, since
+///   "did this specific request just fail" is a more honest signal than a
+///   reachability monitor, and the two can disagree (captive portals,
+///   flaky Wi-Fi). Falls back to the cache only on failure; a live success
+///   always overwrites the cache, so staleness is bounded by "last time this
+///   endpoint actually worked."
+/// - **A small set of writes** (`updateDocument`, `updateCollection`,
+///   pin/star/subscribe create+delete): applied optimistically against the
+///   cache and queued in `OfflineCacheStore`'s `PendingOperation` table on
+///   failure, then replayed in order by `flushPendingOperations()` once back
+///   online. Deliberately doesn't include anything that creates new tree
+///   structure (`createDocument`, `moveDocument`, `archiveDocument`,
+///   `deleteDocument`, `deleteCollection`, `duplicateDocument`) — those need
+///   real server-assigned ids to stay consistent with the rest of the tree,
+///   and reconciling a locally-invented id with the one the server hands
+///   back on sync is a much bigger problem than this pass takes on. Sharing,
+///   permissions, search, and export also stay live-only — read the request,
+///   they need someone else's server session, not just a network.
+/// - **Manual offline mode** (`offlineModeDefaultsKey`): when set, skips
+///   attempting `live` entirely — same fallback/queue paths as a real
+///   failure, just chosen on purpose instead of discovered.
+public actor CachingOutlineAPIClient: OutlineAPIClient {
+    public static let offlineModeDefaultsKey = "outpost.offlineModeEnabled"
+
+    private let live: OutlineAPIClient
+    private let cache: OfflineCacheStore
+    private let defaults: UserDefaults
+    private let encoder: JSONEncoder
+    private let decoder: JSONDecoder
+    private let keyEncoder: JSONEncoder
+
+    public init(live: OutlineAPIClient, cache: OfflineCacheStore, defaults: UserDefaults = .standard) {
+        self.live = live
+        self.cache = cache
+        self.defaults = defaults
+
+        let encoder = JSONEncoder()
+        encoder.dateEncodingStrategy = .iso8601
+        self.encoder = encoder
+
+        let decoder = JSONDecoder()
+        decoder.dateDecodingStrategy = .iso8601
+        self.decoder = decoder
+
+        let keyEncoder = JSONEncoder()
+        keyEncoder.outputFormatting = .sortedKeys
+        self.keyEncoder = keyEncoder
+    }
+
+    private var isManualOfflineModeEnabled: Bool {
+        defaults.bool(forKey: Self.offlineModeDefaultsKey)
+    }
+
+    // MARK: - Cached reads
+
+    public func documentInfo(id: String) async throws -> OutlineDocument {
+        try await cachedFetch(key: "document:\(id)") { try await self.live.documentInfo(id: id) }
+    }
+
+    public func listDocuments(
+        collectionId: String?,
+        parentDocumentId: String?,
+        offset: Int,
+        limit: Int
+    ) async throws -> [OutlineDocument] {
+        let key = "documents:\(collectionId ?? "-"):\(parentDocumentId ?? "-"):\(offset):\(limit)"
+        return try await cachedFetch(key: key) {
+            try await self.live.listDocuments(
+                collectionId: collectionId,
+                parentDocumentId: parentDocumentId,
+                offset: offset,
+                limit: limit
+            )
+        }
+    }
+
+    public func documentsList(_ request: DocumentsListRequest) async throws -> [OutlineDocument] {
+        try await cachedFetch(key: requestKey("documentsList", request)) { try await self.live.documentsList(request) }
+    }
+
+    public func listViewedDocuments(offset: Int, limit: Int) async throws -> [OutlineDocument] {
+        try await cachedFetch(key: "documentsViewed:\(offset):\(limit)") {
+            try await self.live.listViewedDocuments(offset: offset, limit: limit)
+        }
+    }
+
+    public func listCollections(offset: Int, limit: Int) async throws -> [OutlineCollection] {
+        try await cachedFetch(key: "collections:\(offset):\(limit)") {
+            try await self.live.listCollections(offset: offset, limit: limit)
+        }
+    }
+
+    public func collectionInfo(id: String) async throws -> OutlineCollection {
+        try await cachedFetch(key: "collection:\(id)") { try await self.live.collectionInfo(id: id) }
+    }
+
+    // MARK: - Queueable writes
+
+    /// The one exception to "no new tree structure while offline" —
+    /// synthesizes a document under a `pending-<uuid>` id (same scheme as
+    /// pin/star/subscribe), caches it so it's immediately readable/editable,
+    /// and queues the real create. On sync, the server-assigned id replaces
+    /// the placeholder in the cache; anything still referencing the old id
+    /// directly (a currently-open reader, most likely) won't follow that
+    /// rename automatically — a known, narrow limitation, not something this
+    /// pass tries to solve generally.
+    public func createDocument(_ request: CreateDocumentRequest) async throws -> OutlineDocument {
+        if !isManualOfflineModeEnabled {
+            do {
+                let result = try await live.createDocument(request)
+                await cacheDocument(result)
+                return result
+            } catch {
+                return await queueDocumentCreate(request)
+            }
+        }
+        return await queueDocumentCreate(request)
+    }
+
+    public func updateDocument(_ request: UpdateDocumentRequest) async throws -> OutlineDocument {
+        if !isManualOfflineModeEnabled {
+            do {
+                let result = try await live.updateDocument(request)
+                await cacheDocument(result)
+                return result
+            } catch {
+                return try await queueDocumentUpdate(request, dueTo: error)
+            }
+        }
+        return try await queueDocumentUpdate(request, dueTo: nil)
+    }
+
+    public func updateCollection(_ request: UpdateCollectionRequest) async throws -> OutlineCollection {
+        if !isManualOfflineModeEnabled {
+            do {
+                let result = try await live.updateCollection(request)
+                await cacheCollection(result)
+                return result
+            } catch {
+                return try await queueCollectionUpdate(request, dueTo: error)
+            }
+        }
+        return try await queueCollectionUpdate(request, dueTo: nil)
+    }
+
+    public func createPin(_ request: CreatePinRequest) async throws -> OutlinePin {
+        if !isManualOfflineModeEnabled {
+            do { return try await live.createPin(request) } catch { return await queuePinCreate(request) }
+        }
+        return await queuePinCreate(request)
+    }
+
+    public func deletePin(id: String) async throws {
+        if await cancelIfNeverSynced(id: id) { return }
+        if !isManualOfflineModeEnabled {
+            do {
+                try await live.deletePin(id: id)
+                return
+            } catch {
+                await enqueue(.deletePin, payload: IDPayload(id: id), id: "delete-pin-\(id)")
+                return
+            }
+        }
+        await enqueue(.deletePin, payload: IDPayload(id: id), id: "delete-pin-\(id)")
+    }
+
+    public func createSubscription(_ request: CreateSubscriptionRequest) async throws -> OutlineSubscription {
+        if !isManualOfflineModeEnabled {
+            do { return try await live.createSubscription(request) } catch { return await queueSubscriptionCreate(request) }
+        }
+        return await queueSubscriptionCreate(request)
+    }
+
+    public func deleteSubscription(id: String) async throws {
+        if await cancelIfNeverSynced(id: id) { return }
+        if !isManualOfflineModeEnabled {
+            do {
+                try await live.deleteSubscription(id: id)
+                return
+            } catch {
+                await enqueue(.deleteSubscription, payload: IDPayload(id: id), id: "delete-subscription-\(id)")
+                return
+            }
+        }
+        await enqueue(.deleteSubscription, payload: IDPayload(id: id), id: "delete-subscription-\(id)")
+    }
+
+    public func starDocument(_ request: StarDocumentRequest) async throws -> OutlineStar {
+        if !isManualOfflineModeEnabled {
+            do { return try await live.starDocument(request) } catch { return await queueStarDocumentCreate(request) }
+        }
+        return await queueStarDocumentCreate(request)
+    }
+
+    public func starCollection(_ request: StarCollectionRequest) async throws -> OutlineStar {
+        if !isManualOfflineModeEnabled {
+            do { return try await live.starCollection(request) } catch { return await queueStarCollectionCreate(request) }
+        }
+        return await queueStarCollectionCreate(request)
+    }
+
+    public func deleteStar(id: String) async throws {
+        if await cancelIfNeverSynced(id: id) { return }
+        if !isManualOfflineModeEnabled {
+            do {
+                try await live.deleteStar(id: id)
+                return
+            } catch {
+                await enqueue(.deleteStar, payload: IDPayload(id: id), id: "delete-star-\(id)")
+                return
+            }
+        }
+        await enqueue(.deleteStar, payload: IDPayload(id: id), id: "delete-star-\(id)")
+    }
+
+    // MARK: - Pass-through
+
+    public func authInfo() async throws -> OutlineAuthInfo {
+        try await live.authInfo()
+    }
+
+    public func searchDocuments(_ request: DocumentSearchRequest) async throws -> [OutlineDocumentSearchResult] {
+        try await live.searchDocuments(request)
+    }
+
+    public func searchDocumentTitles(_ request: DocumentSearchTitlesRequest) async throws -> [OutlineDocument] {
+        try await live.searchDocumentTitles(request)
+    }
+
+    public func templatizeDocument(_ request: TemplatizeDocumentRequest) async throws -> OutlineTemplate {
+        try await live.templatizeDocument(request)
+    }
+
+    public func duplicateDocument(_ request: DuplicateDocumentRequest) async throws -> [OutlineDocument] {
+        try await live.duplicateDocument(request)
+    }
+
+    public func unpublishDocument(_ request: UnpublishDocumentRequest) async throws -> OutlineDocument {
+        try await live.unpublishDocument(request)
+    }
+
+    public func archiveDocument(id: String) async throws -> OutlineDocument {
+        try await live.archiveDocument(id: id)
+    }
+
+    public func moveDocument(_ request: MoveDocumentRequest) async throws {
+        try await live.moveDocument(request)
+    }
+
+    public func deleteDocument(_ request: DeleteDocumentRequest) async throws {
+        try await live.deleteDocument(request)
+    }
+
+    public func documentInsights(_ request: DocumentInsightsRequest) async throws -> [OutlineDocumentInsight] {
+        try await live.documentInsights(request)
+    }
+
+    public func listRevisions(_ request: ListRevisionsRequest) async throws -> [OutlineRevision] {
+        try await live.listRevisions(request)
+    }
+
+    public func exportDocument(id: String) async throws -> String {
+        try await live.exportDocument(id: id)
+    }
+
+    public func createShare(_ request: CreateShareRequest) async throws -> OutlineShare {
+        try await live.createShare(request)
+    }
+
+    public func shareInfo(documentId: String) async throws -> OutlineShare? {
+        try await live.shareInfo(documentId: documentId)
+    }
+
+    public func updateShare(_ request: UpdateShareRequest) async throws -> OutlineShare {
+        try await live.updateShare(request)
+    }
+
+    public func listShares(_ request: ListSharesRequest) async throws -> [OutlineShare] {
+        try await live.listShares(request)
+    }
+
+    public func revokeShare(id: String) async throws {
+        try await live.revokeShare(id: id)
+    }
+
+    public func listPins(_ request: ListPinsRequest) async throws -> [OutlinePin] {
+        try await live.listPins(request)
+    }
+
+    public func listSubscriptions(_ request: ListSubscriptionsRequest) async throws -> [OutlineSubscription] {
+        try await live.listSubscriptions(request)
+    }
+
+    public func listViews(_ request: ListViewsRequest) async throws -> [OutlineView] {
+        try await live.listViews(request)
+    }
+
+    public func addDocumentUser(_ request: AddDocumentUserRequest) async throws -> OutlineMembership {
+        try await live.addDocumentUser(request)
+    }
+
+    public func removeDocumentUser(_ request: RemoveDocumentUserRequest) async throws {
+        try await live.removeDocumentUser(request)
+    }
+
+    public func documentUsers(_ request: ListDocumentUsersRequest) async throws -> [OutlineDocumentMember] {
+        try await live.documentUsers(request)
+    }
+
+    public func listUsers(_ request: ListUsersRequest) async throws -> [OutlineUser] {
+        try await live.listUsers(request)
+    }
+
+    public func deleteCollection(id: String) async throws {
+        try await live.deleteCollection(id: id)
+    }
+
+    public func exportCollection(_ request: ExportCollectionRequest) async throws -> OutlineFileOperation {
+        try await live.exportCollection(request)
+    }
+
+    public func listStars(_ request: ListStarsRequest) async throws -> [OutlineStar] {
+        try await live.listStars(request)
+    }
+
+    public func currentUser() async throws -> OutlineUser {
+        try await live.currentUser()
+    }
+
+    public func createAttachment(_ request: CreateAttachmentRequest) async throws -> CreateAttachmentResult {
+        try await live.createAttachment(request)
+    }
+
+    public func uploadAttachmentFile(_ result: CreateAttachmentResult, fileData: Data) async throws {
+        try await live.uploadAttachmentFile(result, fileData: fileData)
+    }
+
+    public func deleteAttachment(id: String) async throws {
+        try await live.deleteAttachment(id: id)
+    }
+
+    public func updateUserAvatar(_ request: UpdateUserAvatarRequest) async throws -> OutlineUser {
+        try await live.updateUserAvatar(request)
+    }
+
+    public func updateUserName(_ request: UpdateUserNameRequest) async throws -> OutlineUser {
+        try await live.updateUserName(request)
+    }
+
+    public func updateUserLanguage(_ request: UpdateUserLanguageRequest) async throws -> OutlineUser {
+        try await live.updateUserLanguage(request)
+    }
+
+    public func updateUserPreferences(_ request: UpdateUserPreferencesRequest) async throws -> OutlineUser {
+        try await live.updateUserPreferences(request)
+    }
+
+    public func deleteAccount() async throws {
+        try await live.deleteAccount()
+    }
+
+    public func subscribeToNotifications(eventType: NotificationEventType?) async throws -> OutlineUser {
+        try await live.subscribeToNotifications(eventType: eventType)
+    }
+
+    public func unsubscribeFromNotifications(eventType: NotificationEventType?) async throws -> OutlineUser {
+        try await live.unsubscribeFromNotifications(eventType: eventType)
+    }
+
+    public func listApiKeys(_ request: ListApiKeysRequest) async throws -> [OutlineAPIKey] {
+        try await live.listApiKeys(request)
+    }
+
+    public func createApiKey(_ request: CreateApiKeyRequest) async throws -> OutlineAPIKey {
+        try await live.createApiKey(request)
+    }
+
+    public func deleteApiKey(id: String) async throws {
+        try await live.deleteApiKey(id: id)
+    }
+
+    public func installationInfo() async throws -> OutlineInstallationInfo {
+        try await live.installationInfo()
+    }
+
+    // MARK: - Sync management (Settings surface)
+
+    public func pendingOperations() async -> [PendingOperationSummary] {
+        await cache.pendingOperations().map {
+            PendingOperationSummary(id: $0.id, kind: $0.kind, createdAt: $0.createdAt, attemptCount: $0.attemptCount, lastError: $0.lastError)
+        }
+    }
+
+    public func cacheStorageSummary() async -> CacheStorageSummary {
+        CacheStorageSummary(itemCount: await cache.itemCount(), totalBytes: await cache.totalBytes())
+    }
+
+    public func clearCache() async {
+        await cache.clearAll()
+    }
+
+    /// Replays every queued operation against `live`, in the order they were
+    /// queued. Each is independent — one failing doesn't block the rest.
+    public func flushPendingOperations() async -> SyncFlushSummary {
+        let operations = await cache.pendingOperations()
+        var succeeded = 0
+        var failed = 0
+        for operation in operations {
+            do {
+                try await replay(operation)
+                await cache.removeOperation(id: operation.id)
+                succeeded += 1
+            } catch {
+                await cache.recordFailure(id: operation.id, error: errorDescription(error))
+                failed += 1
+            }
+        }
+        return SyncFlushSummary(succeeded: succeeded, failed: failed)
+    }
+
+    /// "Full Local Sync": eagerly walks every collection and caches every
+    /// document's full content (not just whatever's been opened), so
+    /// browsing offline works for the whole workspace, not only what was
+    /// already viewed. Goes through `self`, not `live`, directly — the
+    /// existing cached-read methods already do the caching as a side effect,
+    /// this just has to drive the walk and separately cache each document by
+    /// id (`listDocuments`'s cache key is the list, not the individual doc).
+    public func performFullSync() async -> FullSyncSummary {
+        var documentsCount = 0
+        var errors: [String] = []
+        var collections: [OutlineCollection] = []
+        var collectionsOffset = 0
+        let collectionsLimit = 100
+        // Outline rejects any `limit` over 100 outright — page in increments
+        // of that instead of guessing a total up front (the protocol doesn't
+        // expose `pagination`'s total count, only the page itself); a page
+        // shorter than the limit is what signals "that was the last one".
+        while true {
+            let page: [OutlineCollection]
+            do {
+                page = try await listCollections(offset: collectionsOffset, limit: collectionsLimit)
+            } catch {
+                errors.append(errorDescription(error))
+                break
+            }
+            collections.append(contentsOf: page)
+            guard page.count == collectionsLimit else { break }
+            collectionsOffset += collectionsLimit
+        }
+
+        for collection in collections {
+            var offset = 0
+            let limit = 100
+            while true {
+                let documents: [OutlineDocument]
+                do {
+                    documents = try await listDocuments(collectionId: collection.id, parentDocumentId: nil, offset: offset, limit: limit)
+                } catch {
+                    errors.append("\(collection.name): \(errorDescription(error))")
+                    break
+                }
+                for document in documents {
+                    await cacheDocument(document)
+                }
+                documentsCount += documents.count
+                guard documents.count == limit else { break }
+                offset += limit
+            }
+        }
+
+        return FullSyncSummary(collectionsCount: collections.count, documentsCount: documentsCount, errors: errors, finishedAt: Date())
+    }
+
+    // MARK: - Helpers
+
+    private func cachedFetch<T: Codable>(key: String, fetch: () async throws -> T) async throws -> T {
+        // Manual offline mode means "skip the network entirely," not just
+        // "prefer it" — without this check, a read would still hit `live`
+        // (and succeed, showing content beyond whatever's cached) any time
+        // the device actually had a connection, defeating the point of
+        // deliberately testing/working as if offline.
+        if isManualOfflineModeEnabled {
+            if let data = await cache.load(forKey: key), let cached = try? decoder.decode(T.self, from: data) {
+                return cached
+            }
+            throw OutlineAPIError.transport(URLError(.notConnectedToInternet))
+        }
+        do {
+            let result = try await fetch()
+            if let data = try? encoder.encode(result) {
+                await cache.save(data, forKey: key)
+            }
+            return result
+        } catch {
+            if let data = await cache.load(forKey: key), let cached = try? decoder.decode(T.self, from: data) {
+                return cached
+            }
+            throw error
+        }
+    }
+
+    private func requestKey(_ prefix: String, _ request: some Encodable) -> String {
+        guard let data = try? keyEncoder.encode(request), let json = String(data: data, encoding: .utf8) else {
+            return prefix
+        }
+        return "\(prefix):\(json)"
+    }
+
+    private func cacheDocument(_ document: OutlineDocument) async {
+        if let data = try? encoder.encode(document) {
+            await cache.save(data, forKey: "document:\(document.id)")
+        }
+    }
+
+    private func cacheCollection(_ collection: OutlineCollection) async {
+        if let data = try? encoder.encode(collection) {
+            await cache.save(data, forKey: "collection:\(collection.id)")
+        }
+    }
+
+    private func enqueue(_ kind: PendingOperationKind, payload: some Encodable, id: String) async {
+        guard let data = try? encoder.encode(payload) else { return }
+        await cache.enqueueOperation(id: id, kind: kind.rawValue, payload: data)
+    }
+
+    /// A delete targeting a `pending-*` id can only mean "cancel the create
+    /// still sitting in the queue" — the server has never heard of that id,
+    /// so queuing the delete would just fail once synced. Returns whether it
+    /// found (and removed) a matching create, meaning the caller is done.
+    private func cancelIfNeverSynced(id: String) async -> Bool {
+        guard id.hasPrefix("pending-") else { return false }
+        return await cache.removeOperation(id: id)
+    }
+
+    private func queueDocumentCreate(_ request: CreateDocumentRequest) async -> OutlineDocument {
+        let pendingId = "pending-\(UUID().uuidString)"
+        let now = Date()
+        let synthesized = OutlineDocument(
+            id: pendingId,
+            title: request.title,
+            text: request.text,
+            emoji: nil,
+            collectionId: request.collectionId,
+            parentDocumentId: request.parentDocumentId,
+            url: "/doc/\(pendingId)",
+            revision: nil,
+            fullWidth: nil,
+            createdAt: now,
+            updatedAt: now,
+            publishedAt: request.publish ? now : nil,
+            archivedAt: nil,
+            deletedAt: nil
+        )
+        await cacheDocument(synthesized)
+        await enqueue(.createDocument, payload: request, id: pendingId)
+        return synthesized
+    }
+
+    private func queueDocumentUpdate(_ request: UpdateDocumentRequest, dueTo error: Error?) async throws -> OutlineDocument {
+        guard let baseData = await cache.load(forKey: "document:\(request.id)"),
+              let base = try? decoder.decode(OutlineDocument.self, from: baseData) else {
+            throw error ?? OutlineAPIError.transport(URLError(.notConnectedToInternet))
+        }
+        let mergedText = request.append == true ? base.text + (request.text ?? "") : (request.text ?? base.text)
+        let merged = OutlineDocument(
+            id: base.id,
+            title: request.title ?? base.title,
+            text: mergedText,
+            emoji: base.emoji,
+            collectionId: base.collectionId,
+            parentDocumentId: base.parentDocumentId,
+            url: base.url,
+            revision: base.revision,
+            fullWidth: request.fullWidth ?? base.fullWidth,
+            createdAt: base.createdAt,
+            updatedAt: Date(),
+            publishedAt: base.publishedAt,
+            archivedAt: base.archivedAt,
+            deletedAt: base.deletedAt
+        )
+        await cacheDocument(merged)
+
+        // Still-unsynced create for this exact document — fold the edit into
+        // the pending create's payload instead of queuing a separate update.
+        // A separate update would target `merged.id`, which is still the
+        // `pending-*` placeholder at replay time; the server has never heard
+        // of it and the update would just fail every retry.
+        if merged.id.hasPrefix("pending-"),
+           let createOp = await cache.pendingOperations().first(where: { $0.id == merged.id && $0.kind == PendingOperationKind.createDocument.rawValue }),
+           let createRequest = try? decoder.decode(CreateDocumentRequest.self, from: createOp.payload) {
+            let resolvedCreate = CreateDocumentRequest(
+                title: merged.title,
+                text: merged.text,
+                collectionId: createRequest.collectionId,
+                parentDocumentId: createRequest.parentDocumentId,
+                publish: createRequest.publish
+            )
+            await enqueue(.createDocument, payload: resolvedCreate, id: merged.id)
+            return merged
+        }
+
+        // Fully resolved (not the original partial request) so replaying just
+        // this one queued operation reproduces `merged` exactly — that's what
+        // makes coalescing a second edit onto the same queued id safe.
+        let resolved = UpdateDocumentRequest(id: merged.id, title: merged.title, text: merged.text, fullWidth: merged.fullWidth)
+        await enqueue(.updateDocument, payload: resolved, id: "update-document-\(merged.id)")
+        return merged
+    }
+
+    private func queueCollectionUpdate(_ request: UpdateCollectionRequest, dueTo error: Error?) async throws -> OutlineCollection {
+        guard let baseData = await cache.load(forKey: "collection:\(request.id)"),
+              let base = try? decoder.decode(OutlineCollection.self, from: baseData) else {
+            throw error ?? OutlineAPIError.transport(URLError(.notConnectedToInternet))
+        }
+        let merged = OutlineCollection(
+            id: base.id,
+            name: request.name ?? base.name,
+            description: request.description ?? base.description,
+            color: base.color,
+            icon: base.icon,
+            createdAt: base.createdAt,
+            updatedAt: Date()
+        )
+        await cacheCollection(merged)
+        let resolved = UpdateCollectionRequest(id: merged.id, name: merged.name, description: merged.description)
+        await enqueue(.updateCollection, payload: resolved, id: "update-collection-\(merged.id)")
+        return merged
+    }
+
+    private func queuePinCreate(_ request: CreatePinRequest) async -> OutlinePin {
+        let pendingId = "pending-\(UUID().uuidString)"
+        await enqueue(.createPin, payload: request, id: pendingId)
+        return OutlinePin(id: pendingId, documentId: request.documentId, collectionId: request.collectionId, index: nil)
+    }
+
+    private func queueSubscriptionCreate(_ request: CreateSubscriptionRequest) async -> OutlineSubscription {
+        let pendingId = "pending-\(UUID().uuidString)"
+        await enqueue(.createSubscription, payload: request, id: pendingId)
+        return OutlineSubscription(id: pendingId, documentId: request.documentId, collectionId: nil, event: request.event)
+    }
+
+    private func queueStarDocumentCreate(_ request: StarDocumentRequest) async -> OutlineStar {
+        let pendingId = "pending-\(UUID().uuidString)"
+        await enqueue(.starDocument, payload: request, id: pendingId)
+        return OutlineStar(id: pendingId, index: nil, documentId: request.documentId, collectionId: nil)
+    }
+
+    private func queueStarCollectionCreate(_ request: StarCollectionRequest) async -> OutlineStar {
+        let pendingId = "pending-\(UUID().uuidString)"
+        await enqueue(.starCollection, payload: request, id: pendingId)
+        return OutlineStar(id: pendingId, index: nil, documentId: nil, collectionId: request.collectionId)
+    }
+
+    private func replay(_ operation: PendingOperation) async throws {
+        guard let kind = PendingOperationKind(rawValue: operation.kind) else {
+            throw OutlineAPIError.decoding(DecodingError.dataCorrupted(
+                DecodingError.Context(codingPath: [], debugDescription: "Unknown pending operation kind: \(operation.kind)")
+            ))
+        }
+        switch kind {
+        case .createDocument:
+            let request = try decoder.decode(CreateDocumentRequest.self, from: operation.payload)
+            let result = try await live.createDocument(request)
+            await cacheDocument(result)
+            // The placeholder id (== operation.id) is now a dead orphan —
+            // nothing server-side will ever answer to it again.
+            await cache.removeCacheEntry(forKey: "document:\(operation.id)")
+        case .updateDocument:
+            let request = try decoder.decode(UpdateDocumentRequest.self, from: operation.payload)
+            let result = try await live.updateDocument(request)
+            await cacheDocument(result)
+        case .updateCollection:
+            let request = try decoder.decode(UpdateCollectionRequest.self, from: operation.payload)
+            let result = try await live.updateCollection(request)
+            await cacheCollection(result)
+        case .createPin:
+            let request = try decoder.decode(CreatePinRequest.self, from: operation.payload)
+            _ = try await live.createPin(request)
+        case .deletePin:
+            let request = try decoder.decode(IDPayload.self, from: operation.payload)
+            try await live.deletePin(id: request.id)
+        case .createSubscription:
+            let request = try decoder.decode(CreateSubscriptionRequest.self, from: operation.payload)
+            _ = try await live.createSubscription(request)
+        case .deleteSubscription:
+            let request = try decoder.decode(IDPayload.self, from: operation.payload)
+            try await live.deleteSubscription(id: request.id)
+        case .starDocument:
+            let request = try decoder.decode(StarDocumentRequest.self, from: operation.payload)
+            _ = try await live.starDocument(request)
+        case .deleteStar:
+            let request = try decoder.decode(IDPayload.self, from: operation.payload)
+            try await live.deleteStar(id: request.id)
+        case .starCollection:
+            let request = try decoder.decode(StarCollectionRequest.self, from: operation.payload)
+            _ = try await live.starCollection(request)
+        }
+    }
+
+    private func errorDescription(_ error: Error) -> String {
+        if let apiError = error as? OutlineAPIError {
+            switch apiError {
+            case .unauthorized: return "Sign-in expired."
+            case .notFound: return "Not found on the server."
+            case .server(let status, let message): return message ?? "Server error (\(status))."
+            case .decoding: return "Unexpected response shape."
+            case .transport: return "Couldn't reach the server."
+            case .tokenUnavailable: return "Couldn't access the saved sign-in."
+            }
+        }
+        return String(describing: error)
+    }
+}

OutlineKit/Sources/OutlineKit/Caching/OfflineCacheStore.swift

@@ -0,0 +1,104 @@
+import Foundation
+import SwiftData
+
+/// Read-through cache backing `CachingOutlineAPIClient` — stores whatever it
+/// last fetched successfully, keyed by request shape, so browsing keeps
+/// working (stale) once the network stops. Also owns the offline write
+/// queue (`PendingOperation`) — same store, same actor, since both need
+/// synchronized access to the same on-disk SwiftData container.
+@ModelActor
+public actor OfflineCacheStore {
+    public static func makeContainer(inMemory: Bool = false) throws -> ModelContainer {
+        let configuration = ModelConfiguration(isStoredInMemoryOnly: inMemory)
+        return try ModelContainer(for: CachedPayload.self, PendingOperation.self, configurations: configuration)
+    }
+
+    // MARK: - Read-through cache
+
+    public func save(_ data: Data, forKey key: String) {
+        let descriptor = FetchDescriptor<CachedPayload>(predicate: #Predicate { $0.key == key })
+        if let existing = try? modelContext.fetch(descriptor).first {
+            existing.payload = data
+            existing.cachedAt = Date()
+        } else {
+            modelContext.insert(CachedPayload(key: key, payload: data, cachedAt: Date()))
+        }
+        try? modelContext.save()
+    }
+
+    public func load(forKey key: String) -> Data? {
+        let descriptor = FetchDescriptor<CachedPayload>(predicate: #Predicate { $0.key == key })
+        return try? modelContext.fetch(descriptor).first?.payload
+    }
+
+    /// Used to drop a temporary `pending-*` document's cache entry once a
+    /// queued create syncs and the server hands back the real id — the
+    /// placeholder key would otherwise sit around as a dead orphan forever.
+    public func removeCacheEntry(forKey key: String) {
+        let descriptor = FetchDescriptor<CachedPayload>(predicate: #Predicate { $0.key == key })
+        guard let existing = try? modelContext.fetch(descriptor).first else { return }
+        modelContext.delete(existing)
+        try? modelContext.save()
+    }
+
+    public func itemCount() -> Int {
+        (try? modelContext.fetchCount(FetchDescriptor<CachedPayload>())) ?? 0
+    }
+
+    public func totalBytes() -> Int {
+        let descriptor = FetchDescriptor<CachedPayload>()
+        let rows = (try? modelContext.fetch(descriptor)) ?? []
+        return rows.reduce(0) { $0 + $1.payload.count }
+    }
+
+    public func clearAll() {
+        let descriptor = FetchDescriptor<CachedPayload>()
+        guard let rows = try? modelContext.fetch(descriptor) else { return }
+        rows.forEach { modelContext.delete($0) }
+        try? modelContext.save()
+    }
+
+    // MARK: - Offline write queue
+
+    /// Upserts by `id` — a second call with the same id (an edit coalescing
+    /// onto a still-unsynced edit, or a create being cancelled by its own
+    /// synthesized id) replaces the row in place rather than piling up.
+    public func enqueueOperation(id: String, kind: String, payload: Data) {
+        let descriptor = FetchDescriptor<PendingOperation>(predicate: #Predicate { $0.id == id })
+        if let existing = try? modelContext.fetch(descriptor).first {
+            existing.kind = kind
+            existing.payload = payload
+            existing.lastError = nil
+            existing.attemptCount = 0
+        } else {
+            modelContext.insert(PendingOperation(id: id, kind: kind, payload: payload, createdAt: Date()))
+        }
+        try? modelContext.save()
+    }
+
+    public func pendingOperations() -> [PendingOperation] {
+        let descriptor = FetchDescriptor<PendingOperation>(sortBy: [SortDescriptor(\.createdAt)])
+        return (try? modelContext.fetch(descriptor)) ?? []
+    }
+
+    /// Returns whether a matching operation was actually found and removed —
+    /// callers use this to detect "this targeted something that never made
+    /// it to the server in the first place" and skip queuing a delete.
+    @discardableResult
+    public func removeOperation(id: String) -> Bool {
+        let descriptor = FetchDescriptor<PendingOperation>(predicate: #Predicate { $0.id == id })
+        guard let existing = try? modelContext.fetch(descriptor).first else { return false }
+        modelContext.delete(existing)
+        try? modelContext.save()
+        return true
+    }
+
+    public func recordFailure(id: String, error: String) {
+        let descriptor = FetchDescriptor<PendingOperation>(predicate: #Predicate { $0.id == id })
+        guard let existing = try? modelContext.fetch(descriptor).first else { return }
+        existing.lastAttemptAt = Date()
+        existing.lastError = error
+        existing.attemptCount += 1
+        try? modelContext.save()
+    }
+}

OutlineKit/Sources/OutlineKit/Caching/PendingOperation.swift

@@ -0,0 +1,40 @@
+import Foundation
+import SwiftData
+
+/// A queued mutation made while offline, waiting to replay against the live
+/// server. `id` is deliberately overloaded: for actions that create a new
+/// server-side record (pin, star, subscription), it's also the synthesized
+/// placeholder id handed back to the caller immediately — so a matching
+/// delete queued before that create ever syncs can cancel both out by id
+/// instead of hitting a server that's never heard of the placeholder. For
+/// actions that edit an existing record (document/collection updates), it's
+/// deterministic per target id, so a second edit before the first syncs
+/// coalesces into one queued operation instead of piling up.
+@Model
+public final class PendingOperation {
+    @Attribute(.unique) public var id: String
+    public var kind: String
+    public var payload: Data
+    public var createdAt: Date
+    public var lastAttemptAt: Date?
+    public var lastError: String?
+    public var attemptCount: Int
+
+    public init(
+        id: String,
+        kind: String,
+        payload: Data,
+        createdAt: Date,
+        lastAttemptAt: Date? = nil,
+        lastError: String? = nil,
+        attemptCount: Int = 0
+    ) {
+        self.id = id
+        self.kind = kind
+        self.payload = payload
+        self.createdAt = createdAt
+        self.lastAttemptAt = lastAttemptAt
+        self.lastError = lastError
+        self.attemptCount = attemptCount
+    }
+}

OutlineKit/Sources/OutlineKit/Caching/SyncTypes.swift

@@ -0,0 +1,50 @@
+import Foundation
+
+/// UI-facing snapshot of a queued offline mutation — deliberately not the
+/// `@Model` type itself, so Settings can display it without holding a
+/// reference into the SwiftData store.
+public struct PendingOperationSummary: Identifiable, Sendable {
+    public let id: String
+    public let kind: String
+    public let createdAt: Date
+    public let attemptCount: Int
+    public let lastError: String?
+}
+
+public struct CacheStorageSummary: Sendable {
+    public let itemCount: Int
+    public let totalBytes: Int
+}
+
+public struct SyncFlushSummary: Sendable {
+    public let succeeded: Int
+    public let failed: Int
+}
+
+public struct FullSyncSummary: Sendable {
+    public let collectionsCount: Int
+    public let documentsCount: Int
+    public let errors: [String]
+    public let finishedAt: Date
+}
+
+/// Every mutation `CachingOutlineAPIClient` knows how to queue offline and
+/// replay later. Deliberately a small, explicit set — see its doc comment
+/// for what's excluded and why.
+enum PendingOperationKind: String, Codable, Sendable {
+    case createDocument
+    case updateDocument
+    case updateCollection
+    case createPin
+    case deletePin
+    case createSubscription
+    case deleteSubscription
+    case starDocument
+    case deleteStar
+    case starCollection
+}
+
+/// Shared payload shape for the delete-by-id queueable operations.
+struct IDPayload: Codable, Sendable {
+    let id: String
+}

OutlineKit/Sources/OutlineKit/Core/OutlineAPIClient.swift

@@ -9,6 +9,10 @@ public protocol OutlineAPIClient: Sendable {
 
     func documentInfo(id: String) async throws -> OutlineDocument
     func listDocuments(collectionId: String?, parentDocumentId: String?, offset: Int, limit: Int) async throws -> [OutlineDocument]
+    /// Richer filtering (sort/direction/userId) for the Home page's tabs. See `DocumentsListRequest`.
+    func documentsList(_ request: DocumentsListRequest) async throws -> [OutlineDocument]
+    /// Documents the current user has recently viewed. Backed by `documents.viewed`.
+    func listViewedDocuments(offset: Int, limit: Int) async throws -> [OutlineDocument]
     /// Full-text search with snippets/ranking. Backed by `documents.search`.
     func searchDocuments(_ request: DocumentSearchRequest) async throws -> [OutlineDocumentSearchResult]
     /// Title-only search — faster, no snippets. Backed by `documents.search_titles`.
@@ -31,6 +35,8 @@ public protocol OutlineAPIClient: Sendable {
     func createShare(_ request: CreateShareRequest) async throws -> OutlineShare
     func shareInfo(documentId: String) async throws -> OutlineShare?
     func updateShare(_ request: UpdateShareRequest) async throws -> OutlineShare
+    func listShares(_ request: ListSharesRequest) async throws -> [OutlineShare]
+    func revokeShare(id: String) async throws
     /// See `OutlinePin` — best-effort, not in the vendored spec.
     func createPin(_ request: CreatePinRequest) async throws -> OutlinePin
     func listPins(_ request: ListPinsRequest) async throws -> [OutlinePin]
@@ -42,6 +48,14 @@ public protocol OutlineAPIClient: Sendable {
     /// Historical view records, not live presence. Backed by `views.list`.
     func listViews(_ request: ListViewsRequest) async throws -> [OutlineView]
 
+    /// See `OutlineMembership`/`OutlineDocumentMember` — `add` is confirmed
+    /// from Outline's official docs, the rest are best-effort.
+    func addDocumentUser(_ request: AddDocumentUserRequest) async throws -> OutlineMembership
+    func removeDocumentUser(_ request: RemoveDocumentUserRequest) async throws
+    func documentUsers(_ request: ListDocumentUsersRequest) async throws -> [OutlineDocumentMember]
+    /// For searching workspace members to invite. Backed by `users.list`.
+    func listUsers(_ request: ListUsersRequest) async throws -> [OutlineUser]
+
     func listCollections(offset: Int, limit: Int) async throws -> [OutlineCollection]
     func collectionInfo(id: String) async throws -> OutlineCollection
     func updateCollection(_ request: UpdateCollectionRequest) async throws -> OutlineCollection
@@ -55,4 +69,40 @@ public protocol OutlineAPIClient: Sendable {
     func deleteStar(id: String) async throws
 
     func currentUser() async throws -> OutlineUser
+
+    /// Two-step presigned upload: this requests where/how to upload,
+    /// `uploadAttachmentFile` performs the actual multipart POST to that
+    /// target. See `OutlineAttachment`/`CreateAttachmentResult`.
+    func createAttachment(_ request: CreateAttachmentRequest) async throws -> CreateAttachmentResult
+    func uploadAttachmentFile(_ result: CreateAttachmentResult, fileData: Data) async throws
+    /// Best-effort — matches the shape every other simple `id`-only delete
+    /// in this API uses (`pins.delete`, `stars.delete`, …), not confirmed
+    /// against a live server specifically for attachments yet.
+    func deleteAttachment(id: String) async throws
+    /// `users.update`, avatar only. See `UpdateUserAvatarRequest`.
+    func updateUserAvatar(_ request: UpdateUserAvatarRequest) async throws -> OutlineUser
+    /// `users.update`, name only. See `UpdateUserNameRequest`.
+    func updateUserName(_ request: UpdateUserNameRequest) async throws -> OutlineUser
+    /// `users.update`, language only. See `UpdateUserLanguageRequest`.
+    func updateUserLanguage(_ request: UpdateUserLanguageRequest) async throws -> OutlineUser
+    /// `users.update`, preferences only. See `UpdateUserPreferencesRequest`.
+    func updateUserPreferences(_ request: UpdateUserPreferencesRequest) async throws -> OutlineUser
+    /// Backed by `users.delete` — self-service account deletion, no
+    /// confirmation code param confirmed live, matches every other simple
+    /// no-body delete in this API.
+    func deleteAccount() async throws
+    /// `nil` targets every notification event. See `NotificationEventType`.
+    func subscribeToNotifications(eventType: NotificationEventType?) async throws -> OutlineUser
+    func unsubscribeFromNotifications(eventType: NotificationEventType?) async throws -> OutlineUser
+
+    /// Settings → API & Access.
+    func listApiKeys(_ request: ListApiKeysRequest) async throws -> [OutlineAPIKey]
+    /// The returned `OutlineAPIKey.value` is the only time the full
+    /// plaintext key is ever available — the caller is responsible for
+    /// displaying it once and then discarding it.
+    func createApiKey(_ request: CreateApiKeyRequest) async throws -> OutlineAPIKey
+    func deleteApiKey(id: String) async throws
+
+    /// Settings → Installation. Self-hosted server version info.
+    func installationInfo() async throws -> OutlineInstallationInfo
 }

OutlineKit/Sources/OutlineKit/LiveOutlineAPIClient.swift

@@ -51,6 +51,14 @@ public actor LiveOutlineAPIClient: OutlineAPIClient {
         )
     }
 
+    public func documentsList(_ request: DocumentsListRequest) async throws -> [OutlineDocument] {
+        try await post("documents.list", body: request)
+    }
+
+    public func listViewedDocuments(offset: Int, limit: Int) async throws -> [OutlineDocument] {
+        try await post("documents.viewed", body: PaginationParams(offset: offset, limit: limit))
+    }
+
     public func searchDocuments(_ request: DocumentSearchRequest) async throws -> [OutlineDocumentSearchResult] {
         try await post("documents.search", body: request)
     }
@@ -113,23 +121,38 @@ public actor LiveOutlineAPIClient: OutlineAPIClient {
     }
 
     public func shareInfo(documentId: String) async throws -> OutlineShare? {
-        do {
+        // Real shape confirmed against a live server: `data` is
-            return try await post("shares.info", body: ShareInfoRequest(documentId: documentId))
+        // `{ shares: [...] }`, not the bare share object the docs imply —
-        } catch OutlineAPIError.notFound {
+        // same pattern as `pins.list`. A document could in principle have
-            return nil
+        // more than one share record; the first is what the reader's
-        }
+        // share sheet cares about.
+        let payload: SharesInfoPayload? = try await postOptional("shares.info", body: ShareInfoRequest(documentId: documentId))
+        return payload?.shares.first
     }
 
     public func updateShare(_ request: UpdateShareRequest) async throws -> OutlineShare {
         try await post("shares.update", body: request)
     }
 
+    public func listShares(_ request: ListSharesRequest) async throws -> [OutlineShare] {
+        try await post("shares.list", body: request)
+    }
+
+    public func revokeShare(id: String) async throws {
+        try await postForSuccess("shares.revoke", body: StarIDParams(id: id))
+    }
+
     public func createPin(_ request: CreatePinRequest) async throws -> OutlinePin {
         try await post("pins.create", body: request)
     }
 
     public func listPins(_ request: ListPinsRequest) async throws -> [OutlinePin] {
-        try await post("pins.list", body: request)
+        // `data` here is `{ pins: [...], documents: [...] }`, not a bare
+        // array — confirmed against a live server. Decoding straight to
+        // `[OutlinePin]` throws on every call, which `try?` at call sites
+        // swallows silently, so pins never showed up anywhere.
+        let payload: PinsListPayload = try await post("pins.list", body: request)
+        return payload.pins
     }
 
     public func deletePin(id: String) async throws {
@@ -152,6 +175,22 @@ public actor LiveOutlineAPIClient: OutlineAPIClient {
         try await post("views.list", body: request)
     }
 
+    public func addDocumentUser(_ request: AddDocumentUserRequest) async throws -> OutlineMembership {
+        try await post("documents.add_user", body: request)
+    }
+
+    public func removeDocumentUser(_ request: RemoveDocumentUserRequest) async throws {
+        try await postForSuccess("documents.remove_user", body: request)
+    }
+
+    public func documentUsers(_ request: ListDocumentUsersRequest) async throws -> [OutlineDocumentMember] {
+        try await post("documents.users", body: request)
+    }
+
+    public func listUsers(_ request: ListUsersRequest) async throws -> [OutlineUser] {
+        try await post("users.list", body: request)
+    }
+
     public func listCollections(offset: Int, limit: Int) async throws -> [OutlineCollection] {
         try await post("collections.list", body: CollectionListParams(offset: offset, limit: limit))
     }
@@ -190,6 +229,103 @@ public actor LiveOutlineAPIClient: OutlineAPIClient {
         try await post("users.info", body: EmptyParams())
     }
 
+    public func createAttachment(_ request: CreateAttachmentRequest) async throws -> CreateAttachmentResult {
+        try await post("attachments.create", body: request)
+    }
+
+    /// No Bearer/CSRF header attached here, deliberately — the presigned
+    /// `form.sig` field (short-lived, scoped to this exact upload key) is
+    /// what authorizes this specific request, the same way an S3 presigned
+    /// POST works. Best-effort against a live server: if it turns out the
+    /// self-hosted local-storage backend also wants a bearer token here,
+    /// that's a one-line addition once confirmed, not a design change.
+    public func uploadAttachmentFile(_ result: CreateAttachmentResult, fileData: Data) async throws {
+        let (body, contentType) = MultipartFormDataBuilder.build(
+            fields: result.form,
+            fileFieldName: "file",
+            fileName: result.attachment.name ?? "avatar",
+            fileData: fileData,
+            fileContentType: result.form["Content-Type"] ?? "application/octet-stream"
+        )
+
+        // `uploadUrl` is a host-relative path (e.g. "/api/files.create") on
+        // a self-hosted local-storage backend, not an absolute S3 URL —
+        // resolving against `baseURL` handles both: `URL(string:relativeTo:)`
+        // replaces the whole path for a leading-slash relative string per
+        // RFC 3986, same resolution already used for user/team avatar URLs.
+        guard let uploadURL = URL(string: result.uploadUrl, relativeTo: baseURL)?.absoluteURL else {
+            throw OutlineAPIError.transport(URLError(.badURL))
+        }
+
+        var request = URLRequest(url: uploadURL)
+        request.httpMethod = "POST"
+        request.setValue(contentType, forHTTPHeaderField: "Content-Type")
+        request.httpBody = body
+
+        let data: Data
+        let response: HTTPURLResponse
+        do {
+            (data, response) = try await httpClient.send(request)
+        } catch let error as OutlineAPIError {
+            throw error
+        } catch {
+            throw OutlineAPIError.transport(error)
+        }
+
+        guard (200...299).contains(response.statusCode) else {
+            let errorEnvelope = try? decoder.decode(OutlineErrorEnvelope.self, from: data)
+            throw OutlineAPIError.server(status: response.statusCode, message: errorEnvelope?.message ?? errorEnvelope?.error)
+        }
+    }
+
+    public func deleteAttachment(id: String) async throws {
+        try await postForSuccess("attachments.delete", body: StarIDParams(id: id))
+    }
+
+    public func updateUserAvatar(_ request: UpdateUserAvatarRequest) async throws -> OutlineUser {
+        try await post("users.update", body: request)
+    }
+
+    public func updateUserName(_ request: UpdateUserNameRequest) async throws -> OutlineUser {
+        try await post("users.update", body: request)
+    }
+
+    public func updateUserLanguage(_ request: UpdateUserLanguageRequest) async throws -> OutlineUser {
+        try await post("users.update", body: request)
+    }
+
+    public func updateUserPreferences(_ request: UpdateUserPreferencesRequest) async throws -> OutlineUser {
+        try await post("users.update", body: request)
+    }
+
+    public func deleteAccount() async throws {
+        try await postForSuccess("users.delete", body: EmptyParams())
+    }
+
+    public func subscribeToNotifications(eventType: NotificationEventType?) async throws -> OutlineUser {
+        try await post("users.notificationsSubscribe", body: NotificationSubscriptionRequest(eventType: eventType?.rawValue))
+    }
+
+    public func unsubscribeFromNotifications(eventType: NotificationEventType?) async throws -> OutlineUser {
+        try await post("users.notificationsUnsubscribe", body: NotificationSubscriptionRequest(eventType: eventType?.rawValue))
+    }
+
+    public func listApiKeys(_ request: ListApiKeysRequest) async throws -> [OutlineAPIKey] {
+        try await post("apiKeys.list", body: request)
+    }
+
+    public func createApiKey(_ request: CreateApiKeyRequest) async throws -> OutlineAPIKey {
+        try await post("apiKeys.create", body: request)
+    }
+
+    public func deleteApiKey(id: String) async throws {
+        try await postForSuccess("apiKeys.delete", body: StarIDParams(id: id))
+    }
+
+    public func installationInfo() async throws -> OutlineInstallationInfo {
+        try await post("installation.info", body: EmptyParams())
+    }
+
     private func post<Body: Encodable, Response: Decodable>(_ path: String, body: Body) async throws -> Response {
         guard let token = try? tokenStore.token() else {
             throw OutlineAPIError.tokenUnavailable
@@ -230,6 +366,52 @@ public actor LiveOutlineAPIClient: OutlineAPIClient {
         }
     }
 
+    /// Like `post(_:body:)`, but for endpoints where "no result" comes back
+    /// as a 200 with a completely empty body instead of a real 404 —
+    /// confirmed against a live server for `shares.info` (no share yet for
+    /// a given document). A 404 is still treated as nil too.
+    private func postOptional<Body: Encodable, Response: Decodable>(_ path: String, body: Body) async throws -> Response? {
+        guard let token = try? tokenStore.token() else {
+            throw OutlineAPIError.tokenUnavailable
+        }
+
+        var request = URLRequest(url: baseURL.appendingPathComponent("api/\(path)"))
+        request.httpMethod = "POST"
+        request.setValue("application/json", forHTTPHeaderField: "Content-Type")
+        request.setValue("Bearer \(token)", forHTTPHeaderField: "Authorization")
+        request.httpBody = try encoder.encode(body)
+
+        let data: Data
+        let response: HTTPURLResponse
+        do {
+            (data, response) = try await httpClient.send(request)
+        } catch let error as OutlineAPIError {
+            throw error
+        } catch {
+            throw OutlineAPIError.transport(error)
+        }
+
+        guard (200...299).contains(response.statusCode) else {
+            let errorEnvelope = try? decoder.decode(OutlineErrorEnvelope.self, from: data)
+            switch response.statusCode {
+            case 401:
+                throw OutlineAPIError.unauthorized
+            case 404:
+                return nil
+            default:
+                throw OutlineAPIError.server(status: response.statusCode, message: errorEnvelope?.message ?? errorEnvelope?.error)
+            }
+        }
+
+        guard !data.isEmpty else { return nil }
+
+        do {
+            return try decoder.decode(OutlineEnvelope<Response>.self, from: data).data
+        } catch {
+            throw OutlineAPIError.decoding(error)
+        }
+    }
+
     /// For endpoints shaped `{ "success": true }` instead of `{ "data": ... }`
     /// (e.g. `collections.delete`) — `post(_:body:)`'s envelope decode doesn't fit.
     private func postForSuccess<Body: Encodable>(_ path: String, body: Body) async throws {
@@ -286,6 +468,15 @@ private struct DuplicateDocumentResponse: Decodable {
     let documents: [OutlineDocument]
 }
 
+private struct PinsListPayload: Decodable {
+    let pins: [OutlinePin]
+    let documents: [OutlineDocument]
+}
+
+private struct SharesInfoPayload: Decodable {
+    let shares: [OutlineShare]
+}
+
 private struct ListStarsResponse: Decodable {
     let stars: [OutlineStar]
 }
@@ -314,6 +505,11 @@ private struct DocumentListParams: Encodable {
     let limit: Int
 }
 
+private struct PaginationParams: Encodable {
+    let offset: Int
+    let limit: Int
+}
+
 private struct CollectionListParams: Encodable {
     let offset: Int
     let limit: Int

OutlineKit/Sources/OutlineKit/Models/NotificationEventType.swift

@@ -0,0 +1,28 @@
+import Foundation
+
+/// The subset of Outline's notification event types this app exposes a
+/// toggle for. Wire values confirmed live (captured `users.update`
+/// responses showing the full `notificationSettings` dictionary after
+/// toggling each one in Outline's own web app). The server tracks more
+/// event types than this app has UI for (`revisions.create`,
+/// `emails.onboarding`, `emails.features` were also seen live) — those are
+/// left alone since `users.notificationsSubscribe`/`Unsubscribe` are
+/// per-event, not a whole-object replace like `preferences`, so there's no
+/// clobbering risk in only covering a subset.
+public enum NotificationEventType: String, CaseIterable, Sendable {
+    case documentPublish = "documents.publish"
+    case documentUpdate = "documents.update"
+    case commentCreate = "comments.create"
+    case commentMentioned = "comments.mentioned"
+    case documentMentioned = "documents.mentioned"
+    case commentGroupMentioned = "comments.group_mentioned"
+    case documentGroupMentioned = "documents.group_mentioned"
+    case commentResolve = "comments.resolve"
+    case reactionCreate = "reactions.create"
+    case collectionCreate = "collections.create"
+    case emailsInviteAccepted = "emails.invite_accepted"
+    case documentAddUser = "documents.add_user"
+    case collectionAddUser = "collections.add_user"
+    case emailsExportCompleted = "emails.export_completed"
+    case accessRequestCreate = "access_requests.create"
+}

OutlineKit/Sources/OutlineKit/Models/OutlineAPIKey.swift

@@ -0,0 +1,40 @@
+import Foundation
+
+/// A personal API key (Settings → API & Access). Only the last 4 characters
+/// of the actual token are ever returned by the server — there's no way to
+/// see a full key again after creation, matching every other API-key UI
+/// convention.
+public struct OutlineAPIKey: Codable, Identifiable, Hashable, Sendable {
+    public let id: String
+    public let name: String
+    public let last4: String?
+    public let scope: [String]?
+    public let createdAt: Date
+    public let expiresAt: Date?
+    public let lastActiveAt: Date?
+    /// The full plaintext key — present *only* in `apiKeys.create`'s
+    /// response, confirmed live: `apiKeys.list` never includes it, matching
+    /// "shown once at creation" being enforced server-side, not just a
+    /// client-side UI convention this app has to uphold on its own.
+    public let value: String?
+
+    public init(
+        id: String,
+        name: String,
+        last4: String? = nil,
+        scope: [String]? = nil,
+        createdAt: Date,
+        expiresAt: Date? = nil,
+        lastActiveAt: Date? = nil,
+        value: String? = nil
+    ) {
+        self.id = id
+        self.name = name
+        self.last4 = last4
+        self.scope = scope
+        self.createdAt = createdAt
+        self.expiresAt = expiresAt
+        self.lastActiveAt = lastActiveAt
+        self.value = value
+    }
+}

OutlineKit/Sources/OutlineKit/Models/OutlineAttachment.swift

@@ -0,0 +1,26 @@
+import Foundation
+
+/// One uploaded file — created via a two-step presigned upload
+/// (`attachments.create` for the upload target, then a direct POST to
+/// `uploadUrl`/`form`). Confirmed live against a self-hosted instance's
+/// local-storage backend; `size` comes back as a string there, not a
+/// number — same "don't trust the vendored spec's implied types" lesson as
+/// everywhere else this codebase has hit it.
+public struct OutlineAttachment: Decodable, Identifiable, Sendable {
+    public let id: String
+    public let documentId: String?
+    public let contentType: String?
+    public let name: String?
+    public let url: String?
+    public let size: String?
+}
+
+/// `attachments.create`'s response — everything needed to perform the
+/// actual upload. `form` fields (Content-Type, key, acl, sig, `_csrf`, …)
+/// must all be included as their own multipart parts, in the same request
+/// as the file itself, POSTed to `uploadUrl`.
+public struct CreateAttachmentResult: Decodable, Sendable {
+    public let attachment: OutlineAttachment
+    public let uploadUrl: String
+    public let form: [String: String]
+}

OutlineKit/Sources/OutlineKit/Models/OutlineInstallationInfo.swift

@@ -0,0 +1,11 @@
+import Foundation
+
+/// `installation.info` — the self-hosted server's own version, confirmed
+/// live. `policies` (a separate top-level array alongside `data` in the raw
+/// response) isn't modeled here — not used by this app's Installation
+/// settings page.
+public struct OutlineInstallationInfo: Decodable, Sendable {
+    public let version: String
+    public let latestVersion: String
+    public let versionsBehind: Int
+}

OutlineKit/Sources/OutlineKit/Models/OutlineMembership.swift

@@ -0,0 +1,31 @@
+import Foundation
+
+/// A user's explicit permission grant on a document, backed by
+/// `documents.add_user`/`documents.remove_user`. Not in the vendored spec —
+/// only `documents.add_user`'s shape is confirmed from Outline's official
+/// docs; `remove` and the response shape here follow the create/delete and
+/// `{data: ...}` conventions used throughout the rest of this API, but
+/// aren't verified against a live server yet.
+public struct OutlineMembership: Decodable, Identifiable, Sendable {
+    public let id: String
+    public let userId: String
+    public let documentId: String?
+    /// `"read"` or `"read_write"` per the documented enum.
+    public let permission: String
+}
+
+/// A workspace member as returned by `documents.users` in the context of a
+/// specific document — same identity fields as `OutlineUser`, plus (if the
+/// server includes it) the permission they hold on that document. Modeled
+/// separately from `OutlineUser` rather than adding an optional field there,
+/// since `permission` only makes sense in this document-scoped context.
+/// Speculative — `documents.users` isn't in the vendored spec, its name is
+/// inferred from Outline's usual `<resource>.<verb>` convention and hasn't
+/// been confirmed against a live server.
+public struct OutlineDocumentMember: Decodable, Identifiable, Sendable {
+    public let id: String
+    public let name: String
+    public let email: String?
+    public let avatarUrl: String?
+    public let permission: String?
+}

OutlineKit/Sources/OutlineKit/Models/OutlinePin.swift

@@ -1,11 +1,11 @@
 import Foundation
 
-/// A document pinned to the top of a collection (or the team home), backed by
+/// A document pinned to the top of a collection, or to team Home when
-/// `pins.*`. Not in the vendored OpenAPI spec (`docs/reference/outline-openapi`)
+/// `collectionId` is `nil`. Backed by `pins.*` — not in the vendored OpenAPI
-/// — that spec has no `Pins` tag at all — but the endpoint exists on Outline's
+/// spec (`docs/reference/outline-openapi`, no `Pins` tag at all), but
-/// actual server (`server/routes/api/pins.ts` upstream). Shape reconstructed
+/// confirmed real against a live server's network traffic. `collectionId: nil`
-/// from general knowledge of Outline's API, not verified against this spec;
+/// is what "Pin to Home" actually sends; a non-nil value is "Pin to
-/// treat field names as best-effort until confirmed against a live server.
+/// Collection", a distinct action.
 public struct OutlinePin: Decodable, Identifiable, Sendable {
     public let id: String
     public let documentId: String

OutlineKit/Sources/OutlineKit/Models/OutlineShare.swift

@@ -1,10 +1,41 @@
 import Foundation
 
 /// A public share link for a document or collection, backed by `shares.*`.
+///
+/// Only `id` and `published` are guaranteed present on every real share
+/// object — everything else is modeled as optional even where the official
+/// API docs don't explicitly mark it nullable, since self-hosted servers
+/// have repeatedly diverged from the hosted app's documented response shape
+/// (see `OutlinePin`'s history) and a single unexpectedly-null field used to
+/// crash this decode entirely ("Got an unexpected response from the
+/// server").
 public struct OutlineShare: Decodable, Identifiable, Sendable {
     public let id: String
+    public let published: Bool
+
     public let documentId: String?
     public let collectionId: String?
-    public let url: String
+    public let documentTitle: String?
-    public let published: Bool
+    public let documentUrl: String?
+    public let sourceTitle: String?
+    public let sourcePath: String?
+    public let urlId: String?
+    public let url: String?
+    public let domain: String?
+    /// Overrides the source document/collection title on the publicly
+    /// shared page, if set.
+    public let title: String?
+    /// Overrides the workspace branding icon on the publicly shared page,
+    /// if set.
+    public let iconUrl: String?
+    public let includeChildDocuments: Bool?
+    public let allowSubscriptions: Bool?
+    public let allowIndexing: Bool?
+    public let showLastUpdated: Bool?
+    public let showTOC: Bool?
+    public let views: Int?
+    public let createdBy: OutlineUser?
+    public let createdAt: Date?
+    public let updatedAt: Date?
+    public let lastAccessedAt: Date?
 }

OutlineKit/Sources/OutlineKit/Models/OutlineUser.swift

@@ -6,18 +6,30 @@ public struct OutlineUser: Codable, Identifiable, Hashable, Sendable {
     public let email: String?
     public let avatarUrl: String?
     public let role: String?
+    public let language: String?
+    public let preferences: OutlineUserPreferences?
+    /// Keyed by `NotificationEventType`'s raw values, plus event types this
+    /// app has no UI for — kept as a flexible dictionary rather than a
+    /// fixed struct for that reason. `true` means subscribed.
+    public let notificationSettings: [String: Bool]?
 
     public init(
         id: String,
         name: String,
         email: String? = nil,
         avatarUrl: String? = nil,
-        role: String? = nil
+        role: String? = nil,
+        language: String? = nil,
+        preferences: OutlineUserPreferences? = nil,
+        notificationSettings: [String: Bool]? = nil
     ) {
         self.id = id
         self.name = name
         self.email = email
         self.avatarUrl = avatarUrl
         self.role = role
+        self.language = language
+        self.preferences = preferences
+        self.notificationSettings = notificationSettings
     }
 }

OutlineKit/Sources/OutlineKit/Models/OutlineUserPreferences.swift

@@ -0,0 +1,109 @@
+import Foundation
+
+/// `User.preferences` — a free-form JSON blob on Outline's own `User` row,
+/// not a fixed-shape API resource. Wire key names below are confirmed
+/// against a live server's own web app traffic (captured toggling every
+/// Preferences setting one at a time), not guessed — see the `CodingKeys`
+/// mapping for the two that don't match this struct's own property names.
+///
+/// The server also validates `preferences` against a known key allowlist
+/// and rejects the whole `users.update` call (not just the bad field) if
+/// any key it doesn't recognize is present — confirmed live via a
+/// `"notificationBadge: Invalid Input"` error when an earlier, wrong value
+/// was sent. That's also why `fullWidthDocuments` is kept here even though
+/// this app has no UI for it yet: this app always sends the *whole*
+/// preferences object back on every save (see
+/// `UpdateUserPreferencesRequest`), so silently dropping an unknown key
+/// during decode would permanently clear it the next time any other
+/// preference here gets saved.
+public struct OutlineUserPreferences: Codable, Hashable, Sendable {
+    public var rememberLastPath: Bool?
+    /// App-facing polarity: `true` means "separate editing mode is on" —
+    /// the opposite of the wire's own `seamlessEdit` (seamless editing and
+    /// separate editing modes are each other's negation), inverted in
+    /// `init(from:)`/`encode(to:)` so nothing outside this file has to
+    /// remember that.
+    public var separateEditing: Bool?
+    public var useCursorPointer: Bool?
+    public var codeBlockLineNumbers: Bool?
+    public var showCommentMarker: Bool?
+    public var smartText: Bool?
+    /// One of `NotificationBadgeStyle`'s raw values.
+    public var notificationBadge: String?
+    /// No UI in this app yet — preserved purely so saving any other
+    /// preference here doesn't clobber it. See the type doc comment.
+    public var fullWidthDocuments: Bool?
+
+    public init(
+        rememberLastPath: Bool? = nil,
+        separateEditing: Bool? = nil,
+        useCursorPointer: Bool? = nil,
+        codeBlockLineNumbers: Bool? = nil,
+        showCommentMarker: Bool? = nil,
+        smartText: Bool? = nil,
+        notificationBadge: String? = nil,
+        fullWidthDocuments: Bool? = nil
+    ) {
+        self.rememberLastPath = rememberLastPath
+        self.separateEditing = separateEditing
+        self.useCursorPointer = useCursorPointer
+        self.codeBlockLineNumbers = codeBlockLineNumbers
+        self.showCommentMarker = showCommentMarker
+        self.smartText = smartText
+        self.notificationBadge = notificationBadge
+        self.fullWidthDocuments = fullWidthDocuments
+    }
+
+    private enum CodingKeys: String, CodingKey {
+        case rememberLastPath
+        case seamlessEdit
+        case useCursorPointer
+        case codeBlockLineNumbers
+        case commentsInGutter
+        case enableSmartText
+        case notificationBadge
+        case fullWidthDocuments
+    }
+
+    public init(from decoder: Decoder) throws {
+        let container = try decoder.container(keyedBy: CodingKeys.self)
+        rememberLastPath = try container.decodeIfPresent(Bool.self, forKey: .rememberLastPath)
+        separateEditing = try container.decodeIfPresent(Bool.self, forKey: .seamlessEdit).map { !$0 }
+        useCursorPointer = try container.decodeIfPresent(Bool.self, forKey: .useCursorPointer)
+        codeBlockLineNumbers = try container.decodeIfPresent(Bool.self, forKey: .codeBlockLineNumbers)
+        showCommentMarker = try container.decodeIfPresent(Bool.self, forKey: .commentsInGutter)
+        smartText = try container.decodeIfPresent(Bool.self, forKey: .enableSmartText)
+        notificationBadge = try container.decodeIfPresent(String.self, forKey: .notificationBadge)
+        fullWidthDocuments = try container.decodeIfPresent(Bool.self, forKey: .fullWidthDocuments)
+    }
+
+    public func encode(to encoder: Encoder) throws {
+        var container = encoder.container(keyedBy: CodingKeys.self)
+        try container.encodeIfPresent(rememberLastPath, forKey: .rememberLastPath)
+        try container.encodeIfPresent(separateEditing.map { !$0 }, forKey: .seamlessEdit)
+        try container.encodeIfPresent(useCursorPointer, forKey: .useCursorPointer)
+        try container.encodeIfPresent(codeBlockLineNumbers, forKey: .codeBlockLineNumbers)
+        try container.encodeIfPresent(showCommentMarker, forKey: .commentsInGutter)
+        try container.encodeIfPresent(smartText, forKey: .enableSmartText)
+        try container.encodeIfPresent(notificationBadge, forKey: .notificationBadge)
+        try container.encodeIfPresent(fullWidthDocuments, forKey: .fullWidthDocuments)
+    }
+}
+
+/// App-icon unread indicator style. Wire values confirmed live (captured
+/// setting all three from Outline's own web app).
+public enum NotificationBadgeStyle: String, CaseIterable, Identifiable, Sendable {
+    case none = "disabled"
+    case unreadIndicator = "indicator"
+    case unreadCount = "count"
+
+    public var id: String { rawValue }
+
+    public var label: String {
+        switch self {
+        case .none: return "None"
+        case .unreadIndicator: return "Unread Indicator"
+        case .unreadCount: return "Unread Count"
+        }
+    }
+}

OutlineKit/Sources/OutlineKit/Networking/MultipartFormDataBuilder.swift

@@ -0,0 +1,40 @@
+import Foundation
+
+/// Builds the multipart/form-data body for Outline's presigned-upload
+/// targets (`attachments.create`'s `uploadUrl`/`form`) — an S3-style
+/// presigned POST: every `form` field has to ride along as its own part in
+/// the same request as the file, not as query params or headers.
+enum MultipartFormDataBuilder {
+    static func build(
+        fields: [String: String],
+        fileFieldName: String,
+        fileName: String,
+        fileData: Data,
+        fileContentType: String,
+        boundary: String = "Boundary-\(UUID().uuidString)"
+    ) -> (body: Data, contentType: String) {
+        var body = Data()
+
+        for (key, value) in fields {
+            body.append("--\(boundary)\r\n".utf8Data)
+            body.append("Content-Disposition: form-data; name=\"\(key)\"\r\n\r\n".utf8Data)
+            body.append(value.utf8Data)
+            body.append("\r\n".utf8Data)
+        }
+
+        body.append("--\(boundary)\r\n".utf8Data)
+        body.append(
+            "Content-Disposition: form-data; name=\"\(fileFieldName)\"; filename=\"\(fileName)\"\r\n".utf8Data
+        )
+        body.append("Content-Type: \(fileContentType)\r\n\r\n".utf8Data)
+        body.append(fileData)
+        body.append("\r\n".utf8Data)
+        body.append("--\(boundary)--\r\n".utf8Data)
+
+        return (body, "multipart/form-data; boundary=\(boundary)")
+    }
+}
+
+private extension String {
+    var utf8Data: Data { Data(utf8) }
+}

OutlineKit/Sources/OutlineKit/Requests/AddDocumentUserRequest.swift

@@ -0,0 +1,16 @@
+import Foundation
+
+/// See `OutlineMembership`. Confirmed shape from Outline's official
+/// `documents.add_user` docs.
+public struct AddDocumentUserRequest: Encodable, Sendable {
+    public let id: String
+    public let userId: String
+    /// `"read"` or `"read_write"`.
+    public let permission: String
+
+    public init(id: String, userId: String, permission: String) {
+        self.id = id
+        self.userId = userId
+        self.permission = permission
+    }
+}

OutlineKit/Sources/OutlineKit/Requests/CreateApiKeyRequest.swift

@@ -0,0 +1,21 @@
+import Foundation
+
+/// `apiKeys.create`. `expiresAt: nil` (the key omitted entirely, not sent as
+/// literal `null`) confirmed live to mean no expiration — Swift's
+/// synthesized `Encodable` already omits `nil` optionals via
+/// `encodeIfPresent`, so no custom `encode(to:)` is needed here the way
+/// `UpdateUserAvatarRequest` needed one for the opposite case.
+public struct CreateApiKeyRequest: Encodable, Sendable {
+    public let name: String
+    public let expiresAt: Date?
+    /// `nil`/omitted grants full access — confirmed live (every key created
+    /// without a scope came back with unrestricted access). A specific
+    /// scope is a list of allowed API paths, e.g. `["/api/documents.info"]`.
+    public let scope: [String]?
+
+    public init(name: String, expiresAt: Date? = nil, scope: [String]? = nil) {
+        self.name = name
+        self.expiresAt = expiresAt
+        self.scope = scope
+    }
+}

OutlineKit/Sources/OutlineKit/Requests/CreateAttachmentRequest.swift

@@ -0,0 +1,19 @@
+import Foundation
+
+/// Requests an upload target for a new file — not the upload itself, see
+/// `OutlineAPIClient.uploadAttachmentFile`. `documentId: nil` is what a
+/// user-avatar upload sends (confirmed live); a real value scopes the
+/// attachment to a document instead (e.g. an inline image embed).
+public struct CreateAttachmentRequest: Encodable, Sendable {
+    public let name: String
+    public let contentType: String
+    public let size: Int
+    public let documentId: String?
+
+    public init(name: String, contentType: String, size: Int, documentId: String? = nil) {
+        self.name = name
+        self.contentType = contentType
+        self.size = size
+        self.documentId = documentId
+    }
+}

OutlineKit/Sources/OutlineKit/Requests/CreateDocumentRequest.swift

@@ -1,6 +1,6 @@
 import Foundation
 
-public struct CreateDocumentRequest: Encodable, Sendable {
+public struct CreateDocumentRequest: Codable, Sendable {
     public let title: String
     public let text: String
     public let collectionId: String

OutlineKit/Sources/OutlineKit/Requests/CreatePinRequest.swift

@@ -1,7 +1,8 @@
 import Foundation
 
-/// See `OutlinePin` — best-effort shape, not in the vendored spec.
+/// See `OutlinePin`. `collectionId: nil` = "Pin to Home", non-nil = "Pin to
-public struct CreatePinRequest: Encodable, Sendable {
+/// Collection" — these are distinct actions on the real server.
+public struct CreatePinRequest: Codable, Sendable {
     public let documentId: String
     public let collectionId: String?
 

OutlineKit/Sources/OutlineKit/Requests/CreateSubscriptionRequest.swift

@@ -1,7 +1,7 @@
 import Foundation
 
 /// See `OutlineSubscription` — best-effort shape, not in the vendored spec.
-public struct CreateSubscriptionRequest: Encodable, Sendable {
+public struct CreateSubscriptionRequest: Codable, Sendable {
     public let documentId: String
     public let event: String
 

OutlineKit/Sources/OutlineKit/Requests/DocumentsListRequest.swift

@@ -0,0 +1,29 @@
+import Foundation
+
+/// Richer `documents.list` query than `OutlineAPIClient.listDocuments` covers
+/// (that one's kept as-is for its existing simple callers) — adds the
+/// sort/direction/userId filters the Home page's tabs need.
+public struct DocumentsListRequest: Encodable, Sendable {
+    public let collectionId: String?
+    public let userId: String?
+    public let sort: String?
+    public let direction: String?
+    public let offset: Int
+    public let limit: Int
+
+    public init(
+        collectionId: String? = nil,
+        userId: String? = nil,
+        sort: String? = nil,
+        direction: String? = nil,
+        offset: Int = 0,
+        limit: Int = 25
+    ) {
+        self.collectionId = collectionId
+        self.userId = userId
+        self.sort = sort
+        self.direction = direction
+        self.offset = offset
+        self.limit = limit
+    }
+}

OutlineKit/Sources/OutlineKit/Requests/ListApiKeysRequest.swift

@@ -0,0 +1,14 @@
+import Foundation
+
+/// `apiKeys.list` — matches every other paginated `.list` endpoint's flat
+/// offset/limit convention (e.g. `ListSharesRequest`), not the nested
+/// `pagination` object that only appears in list *responses*.
+public struct ListApiKeysRequest: Encodable, Sendable {
+    public let offset: Int
+    public let limit: Int
+
+    public init(offset: Int = 0, limit: Int = 25) {
+        self.offset = offset
+        self.limit = limit
+    }
+}

OutlineKit/Sources/OutlineKit/Requests/ListDocumentUsersRequest.swift

@@ -0,0 +1,17 @@
+import Foundation
+
+/// See `OutlineDocumentMember`. Speculative — `documents.users` isn't in
+/// the vendored spec.
+public struct ListDocumentUsersRequest: Encodable, Sendable {
+    public let id: String
+    public let query: String?
+    public let offset: Int
+    public let limit: Int
+
+    public init(id: String, query: String? = nil, offset: Int = 0, limit: Int = 25) {
+        self.id = id
+        self.query = query
+        self.offset = offset
+        self.limit = limit
+    }
+}

OutlineKit/Sources/OutlineKit/Requests/ListPinsRequest.swift

@@ -1,6 +1,6 @@
 import Foundation
 
-/// See `OutlinePin` — best-effort shape, not in the vendored spec.
+/// See `OutlinePin`. `collectionId: nil` lists Home pins only.
 public struct ListPinsRequest: Encodable, Sendable {
     public let collectionId: String?
 

OutlineKit/Sources/OutlineKit/Requests/ListSharesRequest.swift

@@ -0,0 +1,18 @@
+import Foundation
+
+public struct ListSharesRequest: Encodable, Sendable {
+    public let offset: Int
+    public let limit: Int
+    public let sort: String?
+    public let direction: String?
+    /// Filter to shared documents matching a search query.
+    public let query: String?
+
+    public init(offset: Int = 0, limit: Int = 25, sort: String? = nil, direction: String? = nil, query: String? = nil) {
+        self.offset = offset
+        self.limit = limit
+        self.sort = sort
+        self.direction = direction
+        self.query = query
+    }
+}

OutlineKit/Sources/OutlineKit/Requests/ListUsersRequest.swift

@@ -0,0 +1,15 @@
+import Foundation
+
+/// For searching workspace members to invite to a document. Backed by
+/// `users.list`.
+public struct ListUsersRequest: Encodable, Sendable {
+    public let query: String?
+    public let offset: Int
+    public let limit: Int
+
+    public init(query: String? = nil, offset: Int = 0, limit: Int = 25) {
+        self.query = query
+        self.offset = offset
+        self.limit = limit
+    }
+}

OutlineKit/Sources/OutlineKit/Requests/NotificationSubscriptionRequest.swift

@@ -0,0 +1,13 @@
+import Foundation
+
+/// `users.notificationsSubscribe` / `users.notificationsUnsubscribe`. A
+/// `nil` `eventType` targets every notification event at once — confirmed
+/// live via Outline's own "All notifications" master toggle, which sends
+/// no `eventType` at all.
+public struct NotificationSubscriptionRequest: Encodable, Sendable {
+    public let eventType: String?
+
+    public init(eventType: String? = nil) {
+        self.eventType = eventType
+    }
+}

OutlineKit/Sources/OutlineKit/Requests/RemoveDocumentUserRequest.swift

@@ -0,0 +1,14 @@
+import Foundation
+
+/// See `OutlineMembership`. Speculative — follows the create/delete pairing
+/// convention used elsewhere in this API (`documents.add_user` /
+/// `documents.remove_user`), not confirmed against a live server yet.
+public struct RemoveDocumentUserRequest: Encodable, Sendable {
+    public let id: String
+    public let userId: String
+
+    public init(id: String, userId: String) {
+        self.id = id
+        self.userId = userId
+    }
+}

OutlineKit/Sources/OutlineKit/Requests/StarCollectionRequest.swift

@@ -1,6 +1,6 @@
 import Foundation
 
-public struct StarCollectionRequest: Encodable, Sendable {
+public struct StarCollectionRequest: Codable, Sendable {
     public let collectionId: String
 
     public init(collectionId: String) {

OutlineKit/Sources/OutlineKit/Requests/StarDocumentRequest.swift

@@ -1,6 +1,6 @@
 import Foundation
 
-public struct StarDocumentRequest: Encodable, Sendable {
+public struct StarDocumentRequest: Codable, Sendable {
     public let documentId: String
 
     public init(documentId: String) {

OutlineKit/Sources/OutlineKit/Requests/UpdateCollectionRequest.swift

@@ -1,6 +1,6 @@
 import Foundation
 
-public struct UpdateCollectionRequest: Encodable, Sendable {
+public struct UpdateCollectionRequest: Codable, Sendable {
     public let id: String
     public let name: String?
     public let description: String?

OutlineKit/Sources/OutlineKit/Requests/UpdateDocumentRequest.swift

@@ -1,18 +1,12 @@
 import Foundation
 
-public struct UpdateDocumentRequest: Encodable, Sendable {
+public struct UpdateDocumentRequest: Codable, Sendable {
     public let id: String
     public let title: String?
     public let text: String?
     public let append: Bool?
     public let fullWidth: Bool?
     public let insightsEnabled: Bool?
-    /// Not in the vendored spec's `Document`/`documents.update` shape at all
-    /// (only a workspace-level `documentEmbeds` flag exists there) — included
-    /// speculatively since the field may exist on newer self-hosted servers.
-    /// Unrecognized fields are typically ignored server-side rather than
-    /// rejected, so this is low-risk even if unsupported.
-    public let documentEmbeds: Bool?
 
     public init(
         id: String,
@@ -20,8 +14,7 @@ public struct UpdateDocumentRequest: Encodable, Sendable {
         text: String? = nil,
         append: Bool? = nil,
         fullWidth: Bool? = nil,
-        insightsEnabled: Bool? = nil,
+        insightsEnabled: Bool? = nil
-        documentEmbeds: Bool? = nil
     ) {
         self.id = id
         self.title = title
@@ -29,6 +22,5 @@ public struct UpdateDocumentRequest: Encodable, Sendable {
         self.append = append
         self.fullWidth = fullWidth
         self.insightsEnabled = insightsEnabled
-        self.documentEmbeds = documentEmbeds
     }
 }

OutlineKit/Sources/OutlineKit/Requests/UpdateShareRequest.swift

@@ -3,9 +3,16 @@ import Foundation
 public struct UpdateShareRequest: Encodable, Sendable {
     public let id: String
     public let published: Bool
+    /// Overrides the title displayed on the publicly shared page. `nil`
+    /// leaves it unset in the payload (server keeps whatever it already
+    /// has) rather than clearing it — send an empty string to clear.
+    public let title: String?
+    public let iconUrl: String?
 
-    public init(id: String, published: Bool) {
+    public init(id: String, published: Bool, title: String? = nil, iconUrl: String? = nil) {
         self.id = id
         self.published = published
+        self.title = title
+        self.iconUrl = iconUrl
     }
 }

OutlineKit/Sources/OutlineKit/Requests/UpdateUserAvatarRequest.swift

@@ -0,0 +1,28 @@
+import Foundation
+
+/// `users.update`, scoped to just the avatar. Custom `encode(to:)` because
+/// Swift's synthesized `Encodable` uses `encodeIfPresent` for `Optional`
+/// properties, which *omits* the key entirely when the value is `nil` —
+/// removing the avatar needs a literal `"avatarUrl": null` in the request
+/// body, not the key missing. `id` is required: confirmed live (the
+/// captured request body's length only matches `{"id": "...", "avatarUrl":
+/// ...}`, not a shorter shape without it).
+public struct UpdateUserAvatarRequest: Encodable, Sendable {
+    public let id: String
+    public let avatarUrl: String?
+
+    public init(id: String, avatarUrl: String?) {
+        self.id = id
+        self.avatarUrl = avatarUrl
+    }
+
+    private enum CodingKeys: String, CodingKey {
+        case id, avatarUrl
+    }
+
+    public func encode(to encoder: Encoder) throws {
+        var container = encoder.container(keyedBy: CodingKeys.self)
+        try container.encode(id, forKey: .id)
+        try container.encode(avatarUrl, forKey: .avatarUrl)
+    }
+}

OutlineKit/Sources/OutlineKit/Requests/UpdateUserLanguageRequest.swift

@@ -0,0 +1,12 @@
+import Foundation
+
+/// `users.update`, language only.
+public struct UpdateUserLanguageRequest: Encodable, Sendable {
+    public let id: String
+    public let language: String
+
+    public init(id: String, language: String) {
+        self.id = id
+        self.language = language
+    }
+}

OutlineKit/Sources/OutlineKit/Requests/UpdateUserNameRequest.swift

@@ -0,0 +1,12 @@
+import Foundation
+
+/// `users.update`, name only.
+public struct UpdateUserNameRequest: Encodable, Sendable {
+    public let id: String
+    public let name: String
+
+    public init(id: String, name: String) {
+        self.id = id
+        self.name = name
+    }
+}

OutlineKit/Sources/OutlineKit/Requests/UpdateUserPreferencesRequest.swift

@@ -0,0 +1,14 @@
+import Foundation
+
+/// `users.update`, preferences only. Sends the *whole* preferences object
+/// back (not a single changed key) — avoids needing to know whether the
+/// server deep-merges a partial `preferences` body or replaces it outright.
+public struct UpdateUserPreferencesRequest: Encodable, Sendable {
+    public let id: String
+    public let preferences: OutlineUserPreferences
+
+    public init(id: String, preferences: OutlineUserPreferences) {
+        self.id = id
+        self.preferences = preferences
+    }
+}

OutlineKit/Tests/OutlineKitTests/CachingOutlineAPIClientTests.swift

@@ -0,0 +1,514 @@
+import XCTest
+@testable import OutlineKit
+
+private struct NotStubbed: Error {}
+
+/// Conforms to the full protocol (so it can stand in for `live`), but only
+/// the two methods under test in this file have real behavior — everything
+/// else throws loudly if a test accidentally exercises it.
+private final class StubOutlineAPIClient: OutlineAPIClient, @unchecked Sendable {
+    var documentInfoHandler: (@Sendable (String) async throws -> OutlineDocument)?
+    var listCollectionsHandler: (@Sendable (Int, Int) async throws -> [OutlineCollection])?
+    var updateDocumentHandler: (@Sendable (UpdateDocumentRequest) async throws -> OutlineDocument)?
+    var createPinHandler: (@Sendable (CreatePinRequest) async throws -> OutlinePin)?
+    var deletePinHandler: (@Sendable (String) async throws -> Void)?
+    var listDocumentsHandler: (@Sendable (String?, String?, Int, Int) async throws -> [OutlineDocument])?
+    var createDocumentHandler: (@Sendable (CreateDocumentRequest) async throws -> OutlineDocument)?
+
+    func authInfo() async throws -> OutlineAuthInfo { throw NotStubbed() }
+
+    func documentInfo(id: String) async throws -> OutlineDocument {
+        guard let handler = documentInfoHandler else { throw NotStubbed() }
+        return try await handler(id)
+    }
+
+    func listDocuments(collectionId: String?, parentDocumentId: String?, offset: Int, limit: Int) async throws -> [OutlineDocument] {
+        guard let handler = listDocumentsHandler else { throw NotStubbed() }
+        return try await handler(collectionId, parentDocumentId, offset, limit)
+    }
+
+    func documentsList(_ request: DocumentsListRequest) async throws -> [OutlineDocument] { throw NotStubbed() }
+    func listViewedDocuments(offset: Int, limit: Int) async throws -> [OutlineDocument] { throw NotStubbed() }
+    func searchDocuments(_ request: DocumentSearchRequest) async throws -> [OutlineDocumentSearchResult] { throw NotStubbed() }
+    func searchDocumentTitles(_ request: DocumentSearchTitlesRequest) async throws -> [OutlineDocument] { throw NotStubbed() }
+    func createDocument(_ request: CreateDocumentRequest) async throws -> OutlineDocument {
+        guard let handler = createDocumentHandler else { throw NotStubbed() }
+        return try await handler(request)
+    }
+
+    func updateDocument(_ request: UpdateDocumentRequest) async throws -> OutlineDocument {
+        guard let handler = updateDocumentHandler else { throw NotStubbed() }
+        return try await handler(request)
+    }
+
+    func starDocument(_ request: StarDocumentRequest) async throws -> OutlineStar { throw NotStubbed() }
+    func templatizeDocument(_ request: TemplatizeDocumentRequest) async throws -> OutlineTemplate { throw NotStubbed() }
+    func duplicateDocument(_ request: DuplicateDocumentRequest) async throws -> [OutlineDocument] { throw NotStubbed() }
+    func unpublishDocument(_ request: UnpublishDocumentRequest) async throws -> OutlineDocument { throw NotStubbed() }
+    func archiveDocument(id: String) async throws -> OutlineDocument { throw NotStubbed() }
+    func moveDocument(_ request: MoveDocumentRequest) async throws { throw NotStubbed() }
+    func deleteDocument(_ request: DeleteDocumentRequest) async throws { throw NotStubbed() }
+    func documentInsights(_ request: DocumentInsightsRequest) async throws -> [OutlineDocumentInsight] { throw NotStubbed() }
+    func listRevisions(_ request: ListRevisionsRequest) async throws -> [OutlineRevision] { throw NotStubbed() }
+    func exportDocument(id: String) async throws -> String { throw NotStubbed() }
+    func createShare(_ request: CreateShareRequest) async throws -> OutlineShare { throw NotStubbed() }
+    func shareInfo(documentId: String) async throws -> OutlineShare? { throw NotStubbed() }
+    func updateShare(_ request: UpdateShareRequest) async throws -> OutlineShare { throw NotStubbed() }
+    func listShares(_ request: ListSharesRequest) async throws -> [OutlineShare] { throw NotStubbed() }
+    func revokeShare(id: String) async throws { throw NotStubbed() }
+    func createPin(_ request: CreatePinRequest) async throws -> OutlinePin {
+        guard let handler = createPinHandler else { throw NotStubbed() }
+        return try await handler(request)
+    }
+
+    func listPins(_ request: ListPinsRequest) async throws -> [OutlinePin] { throw NotStubbed() }
+
+    func deletePin(id: String) async throws {
+        guard let handler = deletePinHandler else { throw NotStubbed() }
+        try await handler(id)
+    }
+    func createSubscription(_ request: CreateSubscriptionRequest) async throws -> OutlineSubscription { throw NotStubbed() }
+    func listSubscriptions(_ request: ListSubscriptionsRequest) async throws -> [OutlineSubscription] { throw NotStubbed() }
+    func deleteSubscription(id: String) async throws { throw NotStubbed() }
+    func listViews(_ request: ListViewsRequest) async throws -> [OutlineView] { throw NotStubbed() }
+    func addDocumentUser(_ request: AddDocumentUserRequest) async throws -> OutlineMembership { throw NotStubbed() }
+    func removeDocumentUser(_ request: RemoveDocumentUserRequest) async throws { throw NotStubbed() }
+    func documentUsers(_ request: ListDocumentUsersRequest) async throws -> [OutlineDocumentMember] { throw NotStubbed() }
+    func listUsers(_ request: ListUsersRequest) async throws -> [OutlineUser] { throw NotStubbed() }
+
+    func listCollections(offset: Int, limit: Int) async throws -> [OutlineCollection] {
+        guard let handler = listCollectionsHandler else { throw NotStubbed() }
+        return try await handler(offset, limit)
+    }
+
+    func collectionInfo(id: String) async throws -> OutlineCollection { throw NotStubbed() }
+    func updateCollection(_ request: UpdateCollectionRequest) async throws -> OutlineCollection { throw NotStubbed() }
+    func deleteCollection(id: String) async throws { throw NotStubbed() }
+    func exportCollection(_ request: ExportCollectionRequest) async throws -> OutlineFileOperation { throw NotStubbed() }
+    func starCollection(_ request: StarCollectionRequest) async throws -> OutlineStar { throw NotStubbed() }
+    func listStars(_ request: ListStarsRequest) async throws -> [OutlineStar] { throw NotStubbed() }
+    func deleteStar(id: String) async throws { throw NotStubbed() }
+    func currentUser() async throws -> OutlineUser { throw NotStubbed() }
+    func createAttachment(_ request: CreateAttachmentRequest) async throws -> CreateAttachmentResult { throw NotStubbed() }
+    func uploadAttachmentFile(_ result: CreateAttachmentResult, fileData: Data) async throws { throw NotStubbed() }
+    func deleteAttachment(id: String) async throws { throw NotStubbed() }
+    func updateUserAvatar(_ request: UpdateUserAvatarRequest) async throws -> OutlineUser { throw NotStubbed() }
+    func updateUserName(_ request: UpdateUserNameRequest) async throws -> OutlineUser { throw NotStubbed() }
+    func updateUserLanguage(_ request: UpdateUserLanguageRequest) async throws -> OutlineUser { throw NotStubbed() }
+    func updateUserPreferences(_ request: UpdateUserPreferencesRequest) async throws -> OutlineUser { throw NotStubbed() }
+    func deleteAccount() async throws { throw NotStubbed() }
+    func subscribeToNotifications(eventType: NotificationEventType?) async throws -> OutlineUser { throw NotStubbed() }
+    func unsubscribeFromNotifications(eventType: NotificationEventType?) async throws -> OutlineUser { throw NotStubbed() }
+    func listApiKeys(_ request: ListApiKeysRequest) async throws -> [OutlineAPIKey] { throw NotStubbed() }
+    func createApiKey(_ request: CreateApiKeyRequest) async throws -> OutlineAPIKey { throw NotStubbed() }
+    func deleteApiKey(id: String) async throws { throw NotStubbed() }
+    func installationInfo() async throws -> OutlineInstallationInfo { throw NotStubbed() }
+}
+
+private struct StubTransportError: Error {}
+
+final class CachingOutlineAPIClientTests: XCTestCase {
+    private func makeCache() throws -> OfflineCacheStore {
+        OfflineCacheStore(modelContainer: try OfflineCacheStore.makeContainer(inMemory: true))
+    }
+
+    private func makeDocument(id: String = "doc-1", title: String = "Hello") -> OutlineDocument {
+        OutlineDocument(
+            id: id,
+            title: title,
+            text: "body",
+            url: "/doc/\(id)",
+            createdAt: Date(timeIntervalSince1970: 0),
+            updatedAt: Date(timeIntervalSince1970: 0)
+        )
+    }
+
+    private func makeCollection(id: String = "col-1", name: String = "Engineering") -> OutlineCollection {
+        OutlineCollection(
+            id: id,
+            name: name,
+            createdAt: Date(timeIntervalSince1970: 0),
+            updatedAt: Date(timeIntervalSince1970: 0)
+        )
+    }
+
+    func testDocumentInfoWritesThroughToCacheOnSuccess() async throws {
+        let stub = StubOutlineAPIClient()
+        let document = makeDocument()
+        stub.documentInfoHandler = { _ in document }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        let result = try await sut.documentInfo(id: "doc-1")
+
+        XCTAssertEqual(result, document)
+    }
+
+    func testDocumentInfoFallsBackToCacheWhenLiveFails() async throws {
+        let stub = StubOutlineAPIClient()
+        let document = makeDocument()
+        var callCount = 0
+        stub.documentInfoHandler = { _ in
+            callCount += 1
+            if callCount == 1 { return document }
+            throw StubTransportError()
+        }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        // First call succeeds and populates the cache.
+        _ = try await sut.documentInfo(id: "doc-1")
+        // Second call fails live — should transparently return the cached value.
+        let result = try await sut.documentInfo(id: "doc-1")
+
+        XCTAssertEqual(result, document)
+        XCTAssertEqual(callCount, 2)
+    }
+
+    func testDocumentInfoRethrowsWhenLiveFailsAndCacheIsEmpty() async throws {
+        let stub = StubOutlineAPIClient()
+        stub.documentInfoHandler = { _ in throw StubTransportError() }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        do {
+            _ = try await sut.documentInfo(id: "doc-1")
+            XCTFail("Expected an error")
+        } catch is StubTransportError {
+            // expected
+        }
+    }
+
+    func testListCollectionsFallsBackToCacheWhenLiveFails() async throws {
+        let stub = StubOutlineAPIClient()
+        let collections = [makeCollection()]
+        var callCount = 0
+        stub.listCollectionsHandler = { _, _ in
+            callCount += 1
+            if callCount == 1 { return collections }
+            throw StubTransportError()
+        }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        _ = try await sut.listCollections(offset: 0, limit: 25)
+        let result = try await sut.listCollections(offset: 0, limit: 25)
+
+        XCTAssertEqual(result, collections)
+    }
+
+    func testDifferentDocumentIdsAreCachedSeparately() async throws {
+        let stub = StubOutlineAPIClient()
+        let docOne = makeDocument(id: "doc-1", title: "One")
+        let docTwo = makeDocument(id: "doc-2", title: "Two")
+        stub.documentInfoHandler = { id in id == "doc-1" ? docOne : docTwo }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        _ = try await sut.documentInfo(id: "doc-1")
+        _ = try await sut.documentInfo(id: "doc-2")
+        stub.documentInfoHandler = { _ in throw StubTransportError() }
+
+        let cachedOne = try await sut.documentInfo(id: "doc-1")
+        let cachedTwo = try await sut.documentInfo(id: "doc-2")
+
+        XCTAssertEqual(cachedOne, docOne)
+        XCTAssertEqual(cachedTwo, docTwo)
+    }
+
+    // MARK: - Offline writes
+
+    func testUpdateDocumentQueuesAndAppliesOptimisticallyWhenLiveFails() async throws {
+        let stub = StubOutlineAPIClient()
+        let original = makeDocument(id: "doc-1", title: "Original")
+        stub.documentInfoHandler = { _ in original }
+        stub.updateDocumentHandler = { _ in throw StubTransportError() }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        // Populate the cache with the base document first (as a real open would).
+        _ = try await sut.documentInfo(id: "doc-1")
+
+        let updated = try await sut.updateDocument(UpdateDocumentRequest(id: "doc-1", title: "Edited Offline"))
+        XCTAssertEqual(updated.title, "Edited Offline")
+
+        // Re-opening the document (still offline) should reflect the optimistic edit.
+        stub.documentInfoHandler = { _ in throw StubTransportError() }
+        let reopened = try await sut.documentInfo(id: "doc-1")
+        XCTAssertEqual(reopened.title, "Edited Offline")
+
+        let pending = await sut.pendingOperations()
+        XCTAssertEqual(pending.count, 1)
+        XCTAssertEqual(pending.first?.kind, "updateDocument")
+    }
+
+    func testUpdateDocumentRethrowsWhenDocumentWasNeverCached() async throws {
+        let stub = StubOutlineAPIClient()
+        stub.updateDocumentHandler = { _ in throw StubTransportError() }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        do {
+            _ = try await sut.updateDocument(UpdateDocumentRequest(id: "never-seen", title: "x"))
+            XCTFail("Expected an error")
+        } catch is StubTransportError {
+            // expected — nothing to optimistically merge onto
+        }
+    }
+
+    func testSecondOfflineEditCoalescesIntoOneQueuedOperation() async throws {
+        let stub = StubOutlineAPIClient()
+        let original = makeDocument(id: "doc-1", title: "Original")
+        stub.documentInfoHandler = { _ in original }
+        stub.updateDocumentHandler = { _ in throw StubTransportError() }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        _ = try await sut.documentInfo(id: "doc-1")
+        _ = try await sut.updateDocument(UpdateDocumentRequest(id: "doc-1", title: "First Edit"))
+        _ = try await sut.updateDocument(UpdateDocumentRequest(id: "doc-1", title: "Second Edit"))
+
+        let pending = await sut.pendingOperations()
+        XCTAssertEqual(pending.count, 1)
+    }
+
+    func testPinThenUnpinBeforeSyncCancelsOutWithoutQueuingADelete() async throws {
+        let stub = StubOutlineAPIClient()
+        stub.createPinHandler = { _ in throw StubTransportError() }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        let pin = try await sut.createPin(CreatePinRequest(documentId: "doc-1"))
+        XCTAssertTrue(pin.id.hasPrefix("pending-"))
+        let pendingCount1 = await sut.pendingOperations().count
+        XCTAssertEqual(pendingCount1, 1)
+
+        try await sut.deletePin(id: pin.id)
+
+        let pendingCount0 = await sut.pendingOperations().count
+        XCTAssertEqual(pendingCount0, 0)
+    }
+
+    func testFlushPendingOperationsReplaysAndClearsOnSuccess() async throws {
+        let stub = StubOutlineAPIClient()
+        let original = makeDocument(id: "doc-1", title: "Original")
+        stub.documentInfoHandler = { _ in original }
+        stub.updateDocumentHandler = { _ in throw StubTransportError() }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        _ = try await sut.documentInfo(id: "doc-1")
+        _ = try await sut.updateDocument(UpdateDocumentRequest(id: "doc-1", title: "Edited Offline"))
+        let pendingCount1 = await sut.pendingOperations().count
+        XCTAssertEqual(pendingCount1, 1)
+
+        // Network's back — replay should now succeed.
+        stub.updateDocumentHandler = { request in
+            self.makeDocument(id: request.id, title: request.title ?? "")
+        }
+        let summary = await sut.flushPendingOperations()
+
+        XCTAssertEqual(summary.succeeded, 1)
+        XCTAssertEqual(summary.failed, 0)
+        let pendingCount0 = await sut.pendingOperations().count
+        XCTAssertEqual(pendingCount0, 0)
+    }
+
+    func testFlushPendingOperationsRecordsErrorAndKeepsFailedOperation() async throws {
+        let stub = StubOutlineAPIClient()
+        let original = makeDocument(id: "doc-1", title: "Original")
+        stub.documentInfoHandler = { _ in original }
+        stub.updateDocumentHandler = { _ in throw StubTransportError() }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        _ = try await sut.documentInfo(id: "doc-1")
+        _ = try await sut.updateDocument(UpdateDocumentRequest(id: "doc-1", title: "Edited Offline"))
+
+        // Still offline — replay should fail and keep the operation queued.
+        let summary = await sut.flushPendingOperations()
+
+        XCTAssertEqual(summary.succeeded, 0)
+        XCTAssertEqual(summary.failed, 1)
+        let pending = await sut.pendingOperations()
+        XCTAssertEqual(pending.count, 1)
+        XCTAssertEqual(pending.first?.attemptCount, 1)
+        XCTAssertNotNil(pending.first?.lastError)
+    }
+
+    func testManualOfflineModeSkipsLiveEntirely() async throws {
+        let defaults = UserDefaults(suiteName: "CachingOutlineAPIClientTests.manualOffline")!
+        defaults.removePersistentDomain(forName: "CachingOutlineAPIClientTests.manualOffline")
+        defaults.set(true, forKey: CachingOutlineAPIClient.offlineModeDefaultsKey)
+
+        let stub = StubOutlineAPIClient()
+        var liveCallCount = 0
+        stub.createPinHandler = { _ in
+            liveCallCount += 1
+            return OutlinePin(id: "real-id", documentId: "doc-1", collectionId: nil, index: nil)
+        }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache(), defaults: defaults)
+
+        let pin = try await sut.createPin(CreatePinRequest(documentId: "doc-1"))
+
+        XCTAssertEqual(liveCallCount, 0, "Manual offline mode should never attempt the live call")
+        XCTAssertTrue(pin.id.hasPrefix("pending-"))
+    }
+
+    /// Regression test: manual offline mode used to only gate writes —
+    /// reads (listCollections, documentInfo, etc.) still hit `live` first
+    /// any time the device actually had a connection, silently defeating
+    /// "skip the network entirely" for the one thing that mattered most:
+    /// the sidebar showing more than what was actually cached.
+    func testManualOfflineModeSkipsLiveForReadsToo() async throws {
+        let defaults = UserDefaults(suiteName: "CachingOutlineAPIClientTests.manualOfflineReads")!
+        defaults.removePersistentDomain(forName: "CachingOutlineAPIClientTests.manualOfflineReads")
+
+        let stub = StubOutlineAPIClient()
+        let cachedCollection = makeCollection(id: "col-1")
+        var liveCallCount = 0
+        stub.listCollectionsHandler = { _, _ in
+            liveCallCount += 1
+            return [cachedCollection]
+        }
+        let cache = try makeCache()
+        let sut = CachingOutlineAPIClient(live: stub, cache: cache, defaults: defaults)
+
+        // Online first — populates the cache normally.
+        let firstResult = try await sut.listCollections(offset: 0, limit: 25)
+        XCTAssertEqual(firstResult, [cachedCollection])
+        XCTAssertEqual(liveCallCount, 1)
+
+        // Flip manual offline mode on, still "connected" (stub would happily
+        // answer) — the live call must not be attempted at all.
+        defaults.set(true, forKey: CachingOutlineAPIClient.offlineModeDefaultsKey)
+        let secondResult = try await sut.listCollections(offset: 0, limit: 25)
+
+        XCTAssertEqual(secondResult, [cachedCollection])
+        XCTAssertEqual(liveCallCount, 1, "listCollections should have served entirely from cache")
+    }
+
+    func testCacheStorageSummaryReflectsCachedItems() async throws {
+        let stub = StubOutlineAPIClient()
+        stub.documentInfoHandler = { _ in self.makeDocument() }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        _ = try await sut.documentInfo(id: "doc-1")
+        let summary = await sut.cacheStorageSummary()
+
+        XCTAssertEqual(summary.itemCount, 1)
+        XCTAssertGreaterThan(summary.totalBytes, 0)
+
+        await sut.clearCache()
+        let clearedSummary = await sut.cacheStorageSummary()
+        XCTAssertEqual(clearedSummary.itemCount, 0)
+    }
+
+    // MARK: - Full sync
+
+    func testPerformFullSyncNeverRequestsMoreThan100CollectionsPerPage() async throws {
+        let stub = StubOutlineAPIClient()
+        var requestedLimits: [Int] = []
+        // 105 collections across two pages (100 + 5) — regression test for a
+        // real bug: this used to ask for `limit: 250` in one shot, which
+        // Outline's server rejects outright ("Pagination limit is too large
+        // (max 100)"), turning the whole sync into a single silent failure.
+        stub.listCollectionsHandler = { offset, limit in
+            requestedLimits.append(limit)
+            let remaining = max(0, 105 - offset)
+            let count = min(limit, remaining)
+            return (0..<count).map { self.makeCollection(id: "col-\(offset + $0)") }
+        }
+        stub.listDocumentsHandler = { _, _, _, _ in [] }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        let summary = await sut.performFullSync()
+
+        XCTAssertEqual(summary.collectionsCount, 105)
+        XCTAssertTrue(summary.errors.isEmpty)
+        XCTAssertTrue(requestedLimits.allSatisfy { $0 <= 100 }, "requested limits: \(requestedLimits)")
+    }
+
+    func testPerformFullSyncCachesEachDocumentIndividually() async throws {
+        let stub = StubOutlineAPIClient()
+        stub.listCollectionsHandler = { offset, _ in offset == 0 ? [self.makeCollection(id: "col-1")] : [] }
+        stub.listDocumentsHandler = { _, _, offset, _ in
+            offset == 0 ? [self.makeDocument(id: "doc-1"), self.makeDocument(id: "doc-2")] : []
+        }
+        let cache = try makeCache()
+        let sut = CachingOutlineAPIClient(live: stub, cache: cache)
+
+        let summary = await sut.performFullSync()
+        XCTAssertEqual(summary.documentsCount, 2)
+
+        // A plain documentInfo read (no live call available) should now hit
+        // the cache full sync populated, not just the list-shaped cache key.
+        stub.documentInfoHandler = { _ in throw StubTransportError() }
+        let cachedDoc = try await sut.documentInfo(id: "doc-2")
+        XCTAssertEqual(cachedDoc.id, "doc-2")
+    }
+
+    // MARK: - Offline document creation
+
+    func testCreateDocumentQueuesAndReturnsUsableDocumentWhenOffline() async throws {
+        let stub = StubOutlineAPIClient()
+        stub.createDocumentHandler = { _ in throw StubTransportError() }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        let created = try await sut.createDocument(
+            CreateDocumentRequest(title: "New Doc", text: "hello", collectionId: "col-1")
+        )
+
+        XCTAssertTrue(created.id.hasPrefix("pending-"))
+        XCTAssertEqual(created.title, "New Doc")
+        XCTAssertEqual(created.text, "hello")
+
+        // It's immediately readable, same as any other cached document.
+        stub.documentInfoHandler = { _ in throw StubTransportError() }
+        let reopened = try await sut.documentInfo(id: created.id)
+        XCTAssertEqual(reopened.title, "New Doc")
+
+        let pending = await sut.pendingOperations()
+        XCTAssertEqual(pending.count, 1)
+        XCTAssertEqual(pending.first?.kind, "createDocument")
+    }
+
+    func testEditingAnUnsyncedCreatedDocumentFoldsIntoTheCreateInsteadOfQueuingAnUpdate() async throws {
+        let stub = StubOutlineAPIClient()
+        stub.createDocumentHandler = { _ in throw StubTransportError() }
+        stub.updateDocumentHandler = { _ in throw StubTransportError() }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        let created = try await sut.createDocument(
+            CreateDocumentRequest(title: "Untitled", text: "", collectionId: "col-1")
+        )
+        _ = try await sut.updateDocument(UpdateDocumentRequest(id: created.id, title: "Real Title", text: "Real body"))
+
+        let pending = await sut.pendingOperations()
+        XCTAssertEqual(pending.count, 1, "the edit should have folded into the pending create, not added a second operation")
+        XCTAssertEqual(pending.first?.kind, "createDocument")
+
+        stub.documentInfoHandler = { _ in throw StubTransportError() }
+        let reopened = try await sut.documentInfo(id: created.id)
+        XCTAssertEqual(reopened.title, "Real Title")
+        XCTAssertEqual(reopened.text, "Real body")
+    }
+
+    func testFlushingAPendingCreateReconcilesThePlaceholderIdToTheRealOne() async throws {
+        let stub = StubOutlineAPIClient()
+        stub.createDocumentHandler = { _ in throw StubTransportError() }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        let created = try await sut.createDocument(
+            CreateDocumentRequest(title: "New Doc", text: "hello", collectionId: "col-1")
+        )
+        let realDocument = makeDocument(id: "real-server-id", title: "New Doc")
+        stub.createDocumentHandler = { _ in realDocument }
+
+        let summary = await sut.flushPendingOperations()
+        XCTAssertEqual(summary.succeeded, 1)
+        XCTAssertEqual(summary.failed, 0)
+
+        // The real document is now readable under its real id...
+        stub.documentInfoHandler = { _ in throw StubTransportError() }
+        let byRealId = try await sut.documentInfo(id: "real-server-id")
+        XCTAssertEqual(byRealId.id, "real-server-id")
+
+        // ...and the placeholder is gone rather than left as a dead orphan.
+        do {
+            _ = try await sut.documentInfo(id: created.id)
+            XCTFail("Expected the placeholder cache entry to have been removed")
+        } catch {
+            // expected — nothing left under the old id
+        }
+    }
+}

OutlineKit/Tests/OutlineKitTests/LiveOutlineAPIClientTests.swift

@@ -280,6 +280,65 @@ final class LiveOutlineAPIClientTests: XCTestCase {
         XCTAssertEqual(decodedBody.parentDocumentId, "doc-1")
     }
 
+    func testDocumentsListSendsSortDirectionAndUserId() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "data": [] }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        _ = try await client.documentsList(
+            DocumentsListRequest(userId: "user-1", sort: "updatedAt", direction: "DESC")
+        )
+
+        struct SentBody: Decodable {
+            let userId: String?
+            let sort: String?
+            let direction: String?
+        }
+
+        let sentBody = try XCTUnwrap(httpClient.lastRequest?.httpBody)
+        let decodedBody = try JSONDecoder().decode(SentBody.self, from: sentBody)
+        XCTAssertEqual(decodedBody.userId, "user-1")
+        XCTAssertEqual(decodedBody.sort, "updatedAt")
+        XCTAssertEqual(decodedBody.direction, "DESC")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/documents.list")
+    }
+
+    func testListViewedDocumentsDecodesDocuments() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": [
+                {
+                    "id": "doc-1",
+                    "title": "Hello",
+                    "text": "World",
+                    "url": "/doc/hello-doc-1",
+                    "createdAt": "2026-01-01T00:00:00.000Z",
+                    "updatedAt": "2026-01-02T00:00:00.000Z"
+                }
+            ]
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let documents = try await client.listViewedDocuments(offset: 0, limit: 25)
+
+        XCTAssertEqual(documents.first?.id, "doc-1")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/documents.viewed")
+    }
+
     func testDocumentInfoDecodesEnvelopeAndSetsAuthHeader() async throws {
         let httpClient = MockHTTPClient()
         httpClient.responseData = """
@@ -610,6 +669,117 @@ final class LiveOutlineAPIClientTests: XCTestCase {
         XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/shares.create")
     }
 
+    func testShareInfoDecodesRealShareArrayShape() async throws {
+        // Real shape confirmed against a live server — `data` is
+        // `{ shares: [...] }`, not the bare share object the official docs
+        // imply (same pattern as `pins.list`). This is the exact payload
+        // captured for an existing, unpublished share.
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "shares": [
+                    {
+                        "id": "861559ac-906b-4dec-9c1f-3a2d2000745d",
+                        "sourceTitle": "Test Document 3",
+                        "sourcePath": "/doc/test-document-3-VHxABl5RaD",
+                        "collectionId": null,
+                        "documentId": "b1196971-4239-4e35-970f-7fbbc60af044",
+                        "documentTitle": "Test Document 3",
+                        "documentUrl": "/doc/test-document-3-VHxABl5RaD",
+                        "published": false,
+                        "url": "https://docs.psmattas.com/s/861559ac-906b-4dec-9c1f-3a2d2000745d",
+                        "urlId": null,
+                        "createdBy": {
+                            "id": "1e2ef39c-aa82-475b-b5af-d76bb4f023ed",
+                            "name": "Puranjay Savar Mattas",
+                            "avatarUrl": "/api/files.get?key=public/avatar.png",
+                            "color": "#1c9152",
+                            "role": "admin",
+                            "isSuspended": false,
+                            "createdAt": "2025-07-30T17:36:58.560Z",
+                            "updatedAt": "2026-08-14T16:47:45.037Z",
+                            "deletedAt": null,
+                            "lastActiveAt": "2026-08-14T16:47:45.037Z",
+                            "timezone": "Europe/Dublin"
+                        },
+                        "includeChildDocuments": false,
+                        "allowIndexing": false,
+                        "allowSubscriptions": true,
+                        "showLastUpdated": false,
+                        "showTOC": false,
+                        "title": null,
+                        "iconUrl": null,
+                        "views": 0,
+                        "domain": null,
+                        "createdAt": "2026-08-14T16:49:40.146Z",
+                        "updatedAt": "2026-08-14T16:49:40.146Z"
+                    }
+                ]
+            },
+            "policies": [
+                { "id": "861559ac-906b-4dec-9c1f-3a2d2000745d", "abilities": { "read": true, "update": false, "revoke": true } }
+            ],
+            "status": 200,
+            "ok": true
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let share = try await client.shareInfo(documentId: "doc-1")
+
+        XCTAssertEqual(share?.id, "861559ac-906b-4dec-9c1f-3a2d2000745d")
+        XCTAssertEqual(share?.published, false)
+        XCTAssertEqual(share?.views, 0)
+        XCTAssertEqual(share?.createdBy?.name, "Puranjay Savar Mattas")
+        XCTAssertEqual(share?.documentId, "b1196971-4239-4e35-970f-7fbbc60af044")
+    }
+
+    func testListSharesDecodesSharesArray() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": [
+                { "id": "share-1", "documentId": "doc-1", "collectionId": null, "url": "https://outline.example.com/s/share-1", "published": true }
+            ],
+            "pagination": { "offset": 0, "limit": 25 }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let shares = try await client.listShares(ListSharesRequest())
+
+        XCTAssertEqual(shares.first?.id, "share-1")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/shares.list")
+    }
+
+    func testRevokeShareSendsRequest() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "success": true }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        try await client.revokeShare(id: "share-1")
+
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/shares.revoke")
+    }
+
     func testShareInfoReturnsNilOnNotFound() async throws {
         let httpClient = MockHTTPClient()
         httpClient.statusCode = 404
@@ -628,6 +798,24 @@ final class LiveOutlineAPIClientTests: XCTestCase {
         XCTAssertNil(share)
     }
 
+    func testShareInfoReturnsNilOnEmptyBody() async throws {
+        // Confirmed against a live server: shares.info returns a 200 with a
+        // completely empty body (not a 404) when no share exists yet for a
+        // given document.
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = Data()
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let share = try await client.shareInfo(documentId: "doc-1")
+
+        XCTAssertNil(share)
+    }
+
     func testListViewsDecodesViewsAndFiltersNilLastViewedAt() async throws {
         let httpClient = MockHTTPClient()
         httpClient.responseData = """
@@ -676,6 +864,34 @@ final class LiveOutlineAPIClientTests: XCTestCase {
         XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/pins.create")
     }
 
+    func testListPinsDecodesNestedPinsArray() async throws {
+        // Real shape confirmed against a live server: `data` is
+        // `{ pins: [...], documents: [...] }`, not a bare array.
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "pagination": { "limit": 25, "offset": 0 },
+            "data": {
+                "pins": [
+                    { "id": "pin-1", "documentId": "doc-1", "collectionId": null, "index": "h" }
+                ],
+                "documents": []
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let pins = try await client.listPins(ListPinsRequest(collectionId: nil))
+
+        XCTAssertEqual(pins.first?.id, "pin-1")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/pins.list")
+    }
+
     func testCreateSubscriptionDecodesSubscription() async throws {
         let httpClient = MockHTTPClient()
         httpClient.responseData = """
@@ -694,6 +910,573 @@ final class LiveOutlineAPIClientTests: XCTestCase {
         XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/subscriptions.create")
     }
 
+    func testAddDocumentUserDecodesMembership() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "data": { "id": "mem-1", "userId": "user-1", "documentId": "doc-1", "permission": "read" } }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let membership = try await client.addDocumentUser(
+            AddDocumentUserRequest(id: "doc-1", userId: "user-1", permission: "read")
+        )
+
+        XCTAssertEqual(membership.id, "mem-1")
+        XCTAssertEqual(membership.permission, "read")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/documents.add_user")
+    }
+
+    func testRemoveDocumentUserSendsRequest() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "success": true }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        try await client.removeDocumentUser(RemoveDocumentUserRequest(id: "doc-1", userId: "user-1"))
+
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/documents.remove_user")
+    }
+
+    func testDocumentUsersDecodesMembersArray() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": [
+                { "id": "user-1", "name": "Jane Doe", "email": "jane@example.com", "avatarUrl": null, "permission": "read_write" }
+            ]
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let members = try await client.documentUsers(ListDocumentUsersRequest(id: "doc-1"))
+
+        XCTAssertEqual(members.first?.name, "Jane Doe")
+        XCTAssertEqual(members.first?.permission, "read_write")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/documents.users")
+    }
+
+    func testListUsersDecodesUsersArray() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": [
+                { "id": "user-1", "name": "Jane Doe", "email": "jane@example.com", "role": "member" }
+            ]
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let users = try await client.listUsers(ListUsersRequest(query: "Jane"))
+
+        XCTAssertEqual(users.first?.name, "Jane Doe")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/users.list")
+    }
+
+    func testUpdateUserAvatarSendsExplicitNullWhenRemoving() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "user-1",
+                "name": "Jane Doe",
+                "avatarUrl": null
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let user = try await client.updateUserAvatar(UpdateUserAvatarRequest(id: "user-1", avatarUrl: nil))
+
+        XCTAssertNil(user.avatarUrl)
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/users.update")
+        let sentBody = try XCTUnwrap(httpClient.lastRequest?.httpBody)
+        let sentJSON = try XCTUnwrap(String(data: sentBody, encoding: .utf8))
+        // The whole point of UpdateUserAvatarRequest's custom encode(to:) —
+        // Swift's synthesized Encodable would have omitted the key entirely
+        // for a nil Optional instead of sending a literal null.
+        XCTAssertTrue(sentJSON.contains("\"avatarUrl\":null"), "expected an explicit null, got: \(sentJSON)")
+    }
+
+    func testUpdateUserAvatarSendsTheNewURLWhenSet() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "user-1",
+                "name": "Jane Doe",
+                "avatarUrl": "/api/attachments.redirect?id=abc"
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let user = try await client.updateUserAvatar(
+            UpdateUserAvatarRequest(id: "user-1", avatarUrl: "/api/attachments.redirect?id=abc")
+        )
+
+        XCTAssertEqual(user.avatarUrl, "/api/attachments.redirect?id=abc")
+        let sentBody = try XCTUnwrap(httpClient.lastRequest?.httpBody)
+        let sentJSON = try XCTUnwrap(String(data: sentBody, encoding: .utf8))
+        XCTAssertTrue(sentJSON.contains("\"id\":\"user-1\""))
+    }
+
+    func testUpdateUserNameSendsRequestAndDecodesResult() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "user-1",
+                "name": "New Name"
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let user = try await client.updateUserName(UpdateUserNameRequest(id: "user-1", name: "New Name"))
+
+        XCTAssertEqual(user.name, "New Name")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/users.update")
+    }
+
+    func testUpdateUserLanguageSendsRequestAndDecodesResult() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "user-1",
+                "name": "Jane Doe",
+                "language": "fr_FR"
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let user = try await client.updateUserLanguage(UpdateUserLanguageRequest(id: "user-1", language: "fr_FR"))
+
+        XCTAssertEqual(user.language, "fr_FR")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/users.update")
+    }
+
+    func testUpdateUserPreferencesSendsWholeObjectAndDecodesResult() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "user-1",
+                "name": "Jane Doe",
+                "preferences": { "rememberLastPath": true, "useCursorPointer": true }
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let preferences = OutlineUserPreferences(rememberLastPath: true, useCursorPointer: true)
+        let user = try await client.updateUserPreferences(UpdateUserPreferencesRequest(id: "user-1", preferences: preferences))
+
+        XCTAssertEqual(user.preferences?.rememberLastPath, true)
+        XCTAssertEqual(user.preferences?.useCursorPointer, true)
+
+        let sentBody = try JSONSerialization.jsonObject(with: httpClient.lastRequest!.httpBody!) as? [String: Any]
+        let sentPreferences = sentBody?["preferences"] as? [String: Any]
+        XCTAssertEqual(sentPreferences?["rememberLastPath"] as? Bool, true)
+        XCTAssertEqual(sentPreferences?["useCursorPointer"] as? Bool, true)
+    }
+
+    /// Locks in the wire mapping confirmed against a live server's own web
+    /// app traffic: `seamlessEdit`/`commentsInGutter`/`enableSmartText` are
+    /// the real keys (not `separateEditing`/`showCommentMarker`/`smartText`
+    /// this struct exposes), and `seamlessEdit` is the *negation* of this
+    /// app's `separateEditing`.
+    func testOutlineUserPreferencesDecodesRealWireKeys() throws {
+        let json = """
+        {
+            "seamlessEdit": false,
+            "commentsInGutter": true,
+            "enableSmartText": true,
+            "rememberLastPath": true,
+            "useCursorPointer": true,
+            "codeBlockLineNumbers": false,
+            "notificationBadge": "indicator",
+            "fullWidthDocuments": true
+        }
+        """.data(using: .utf8)!
+
+        let preferences = try JSONDecoder().decode(OutlineUserPreferences.self, from: json)
+
+        XCTAssertEqual(preferences.separateEditing, true, "seamlessEdit: false means separate editing is ON")
+        XCTAssertEqual(preferences.showCommentMarker, true)
+        XCTAssertEqual(preferences.smartText, true)
+        XCTAssertEqual(preferences.rememberLastPath, true)
+        XCTAssertEqual(preferences.useCursorPointer, true)
+        XCTAssertEqual(preferences.codeBlockLineNumbers, false)
+        XCTAssertEqual(preferences.notificationBadge, "indicator")
+        XCTAssertEqual(preferences.fullWidthDocuments, true)
+    }
+
+    func testOutlineUserPreferencesEncodesRealWireKeysAndInvertsSeparateEditing() throws {
+        var preferences = OutlineUserPreferences()
+        preferences.separateEditing = true
+        preferences.showCommentMarker = false
+        preferences.smartText = true
+        preferences.fullWidthDocuments = true
+
+        let data = try JSONEncoder().encode(preferences)
+        let object = try JSONSerialization.jsonObject(with: data) as? [String: Any]
+
+        XCTAssertEqual(object?["seamlessEdit"] as? Bool, false, "separateEditing: true must encode as seamlessEdit: false")
+        XCTAssertEqual(object?["commentsInGutter"] as? Bool, false)
+        XCTAssertEqual(object?["enableSmartText"] as? Bool, true)
+        XCTAssertEqual(object?["fullWidthDocuments"] as? Bool, true)
+        XCTAssertNil(object?["separateEditing"], "must not leak this app's own field name onto the wire")
+        XCTAssertNil(object?["showCommentMarker"])
+        XCTAssertNil(object?["smartText"])
+    }
+
+    func testSubscribeToNotificationsSendsEventTypeAndDecodesResult() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "user-1",
+                "name": "Jane Doe",
+                "notificationSettings": { "documents.publish": true }
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let user = try await client.subscribeToNotifications(eventType: .documentPublish)
+
+        XCTAssertEqual(user.notificationSettings?["documents.publish"], true)
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/users.notificationsSubscribe")
+        let sentBody = try JSONSerialization.jsonObject(with: httpClient.lastRequest!.httpBody!) as? [String: Any]
+        XCTAssertEqual(sentBody?["eventType"] as? String, "documents.publish")
+    }
+
+    func testUnsubscribeFromNotificationsWithNilEventTypeTargetsAll() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "user-1",
+                "name": "Jane Doe",
+                "notificationSettings": { "documents.publish": false }
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        _ = try await client.unsubscribeFromNotifications(eventType: nil)
+
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/users.notificationsUnsubscribe")
+        let sentBody = try JSONSerialization.jsonObject(with: httpClient.lastRequest!.httpBody!) as? [String: Any]
+        XCTAssertNil(sentBody?["eventType"])
+    }
+
+    func testListApiKeysDecodesResult() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "pagination": { "limit": 25, "offset": 0 },
+            "data": [
+                {
+                    "id": "c3eec545-6d38-4065-90dc-b6c96a551445",
+                    "name": "Outpost",
+                    "scope": null,
+                    "last4": "dl1h",
+                    "createdAt": "2026-08-12T18:44:32.467Z",
+                    "updatedAt": "2026-08-12T18:44:32.467Z",
+                    "expiresAt": null,
+                    "lastActiveAt": "2026-08-18T01:01:36.553Z"
+                }
+            ]
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let keys = try await client.listApiKeys(ListApiKeysRequest())
+
+        XCTAssertEqual(keys.count, 1)
+        XCTAssertEqual(keys.first?.name, "Outpost")
+        XCTAssertEqual(keys.first?.last4, "dl1h")
+        XCTAssertNil(keys.first?.expiresAt)
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/apiKeys.list")
+    }
+
+    func testInstallationInfoDecodesResult() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": { "version": "1.9.2", "latestVersion": "1.9.2", "versionsBehind": 0 },
+            "policies": []
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let info = try await client.installationInfo()
+
+        XCTAssertEqual(info.version, "1.9.2")
+        XCTAssertEqual(info.versionsBehind, 0)
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/installation.info")
+    }
+
+    func testCreateApiKeyOmitsExpiresAtWhenNilAndDecodesValue() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "5655fb3e-2a8c-4f2c-9cae-bbd910ef8683",
+                "name": "test",
+                "scope": null,
+                "value": "ol_api_Xqx9Jti7xUunb5b8bXh29vHmBngqjJl3Id0DGv",
+                "last4": "0DGv",
+                "createdAt": "2026-08-18T15:39:29.872Z",
+                "expiresAt": null,
+                "lastActiveAt": null
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let key = try await client.createApiKey(CreateApiKeyRequest(name: "test"))
+
+        XCTAssertEqual(key.value, "ol_api_Xqx9Jti7xUunb5b8bXh29vHmBngqjJl3Id0DGv")
+        XCTAssertNil(key.expiresAt)
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/apiKeys.create")
+        let sentBody = try JSONSerialization.jsonObject(with: httpClient.lastRequest!.httpBody!) as? [String: Any]
+        XCTAssertEqual(sentBody?["name"] as? String, "test")
+        XCTAssertNil(sentBody?["expiresAt"], "omitting expiresAt (not sending null) is what produces a non-expiring key")
+        XCTAssertNil(sentBody?["scope"])
+    }
+
+    func testCreateApiKeySendsExpiresAtWhenProvided() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "04e204fb-51a4-4b54-aed1-2056dfd576d7",
+                "name": "Test",
+                "scope": null,
+                "value": "ol_api_aeYcOts7I2sJXw3zaztjydRM3W3W89TBAtcLts",
+                "last4": "cLts",
+                "createdAt": "2026-08-18T15:38:22.928Z",
+                "expiresAt": "2026-11-16T23:59:59.999Z",
+                "lastActiveAt": null
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let expiresAt = Date(timeIntervalSince1970: 1_795_000_000)
+        _ = try await client.createApiKey(CreateApiKeyRequest(name: "Test", expiresAt: expiresAt))
+
+        let sentBody = try JSONSerialization.jsonObject(with: httpClient.lastRequest!.httpBody!) as? [String: Any]
+        XCTAssertNotNil(sentBody?["expiresAt"])
+    }
+
+    func testDeleteApiKeySendsRequest() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "success": true }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        try await client.deleteApiKey(id: "5655fb3e-2a8c-4f2c-9cae-bbd910ef8683")
+
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/apiKeys.delete")
+        let sentBody = try JSONSerialization.jsonObject(with: httpClient.lastRequest!.httpBody!) as? [String: Any]
+        XCTAssertEqual(sentBody?["id"] as? String, "5655fb3e-2a8c-4f2c-9cae-bbd910ef8683")
+    }
+
+    func testDeleteAccountSendsRequest() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "success": true }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        try await client.deleteAccount()
+
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/users.delete")
+    }
+
+    func testDeleteAttachmentSendsRequest() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "success": true }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        try await client.deleteAttachment(id: "attach-1")
+
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/attachments.delete")
+    }
+
+    func testCreateAttachmentDecodesUploadTargetAndFormFields() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "attachment": {
+                    "id": "attach-1",
+                    "documentId": null,
+                    "contentType": "image/jpeg",
+                    "name": "avatar.jpg",
+                    "url": "/api/attachments.redirect?id=attach-1",
+                    "size": "59304"
+                },
+                "uploadUrl": "/api/files.create",
+                "form": {
+                    "Content-Type": "image/jpeg",
+                    "key": "uploads/user-1/attach-1/avatar.jpg",
+                    "acl": "public-read"
+                }
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let result = try await client.createAttachment(
+            CreateAttachmentRequest(name: "avatar.jpg", contentType: "image/jpeg", size: 59304)
+        )
+
+        XCTAssertEqual(result.attachment.id, "attach-1")
+        XCTAssertEqual(result.attachment.size, "59304")
+        XCTAssertEqual(result.uploadUrl, "/api/files.create")
+        XCTAssertEqual(result.form["acl"], "public-read")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/attachments.create")
+    }
+
+    func testUploadAttachmentFilePostsToTheResolvedRelativeURL() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "success": true }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let uploadTarget = CreateAttachmentResult(
+            attachment: OutlineAttachment(
+                id: "attach-1",
+                documentId: nil,
+                contentType: "image/jpeg",
+                name: "avatar.jpg",
+                url: "/api/attachments.redirect?id=attach-1",
+                size: "3"
+            ),
+            uploadUrl: "/api/files.create",
+            form: ["Content-Type": "image/jpeg", "key": "uploads/attach-1"]
+        )
+
+        try await client.uploadAttachmentFile(uploadTarget, fileData: Data("abc".utf8))
+
+        // Resolved against baseURL's host, not appended onto "/api/<baseURL-relative-path>".
+        XCTAssertEqual(httpClient.lastRequest?.url?.absoluteString, "https://outline.example.com/api/files.create")
+        XCTAssertNil(httpClient.lastRequest?.value(forHTTPHeaderField: "Authorization"))
+        let contentType = httpClient.lastRequest?.value(forHTTPHeaderField: "Content-Type")
+        XCTAssertTrue(contentType?.hasPrefix("multipart/form-data; boundary=") ?? false)
+    }
+
     func testMissingTokenThrowsTokenUnavailable() async throws {
         let httpClient = MockHTTPClient()
         let client = LiveOutlineAPIClient(

OutlineKit/Tests/OutlineKitTests/MultipartFormDataBuilderTests.swift

@@ -0,0 +1,48 @@
+import XCTest
+@testable import OutlineKit
+
+final class MultipartFormDataBuilderTests: XCTestCase {
+    func testBuildIncludesEveryFieldAndTheFile() throws {
+        let fileData = Data("fake-jpeg-bytes".utf8)
+        let (body, contentType) = MultipartFormDataBuilder.build(
+            fields: ["key": "uploads/abc", "acl": "public-read", "Content-Type": "image/jpeg"],
+            fileFieldName: "file",
+            fileName: "avatar.jpg",
+            fileData: fileData,
+            fileContentType: "image/jpeg",
+            boundary: "TestBoundary"
+        )
+
+        let bodyString = String(decoding: body, as: UTF8.self)
+
+        XCTAssertEqual(contentType, "multipart/form-data; boundary=TestBoundary")
+        XCTAssertTrue(bodyString.contains("Content-Disposition: form-data; name=\"key\""))
+        XCTAssertTrue(bodyString.contains("uploads/abc"))
+        XCTAssertTrue(bodyString.contains("Content-Disposition: form-data; name=\"acl\""))
+        XCTAssertTrue(bodyString.contains("public-read"))
+        XCTAssertTrue(bodyString.contains("Content-Disposition: form-data; name=\"file\"; filename=\"avatar.jpg\""))
+        XCTAssertTrue(bodyString.contains("fake-jpeg-bytes"))
+        XCTAssertTrue(bodyString.hasPrefix("--TestBoundary\r\n"))
+        XCTAssertTrue(bodyString.hasSuffix("--TestBoundary--\r\n"))
+    }
+
+    func testFileFieldComesAfterAllFormFields() throws {
+        let (body, _) = MultipartFormDataBuilder.build(
+            fields: ["a": "1", "b": "2"],
+            fileFieldName: "file",
+            fileName: "x.jpg",
+            fileData: Data("bytes".utf8),
+            fileContentType: "image/jpeg",
+            boundary: "B"
+        )
+        let bodyString = String(decoding: body, as: UTF8.self)
+
+        let fieldsRange = bodyString.range(of: "name=\"a\"")
+        let fileRange = bodyString.range(of: "name=\"file\"")
+        XCTAssertNotNil(fieldsRange)
+        XCTAssertNotNil(fileRange)
+        if let fieldsRange, let fileRange {
+            XCTAssertTrue(fieldsRange.lowerBound < fileRange.lowerBound)
+        }
+    }
+}

Outpost.xcodeproj/project.pbxproj

@@ -299,7 +299,7 @@
 				CLANG_WARN__DUPLICATE_METHOD_MATCH = YES;
 				COPY_PHASE_STRIP = NO;
 				DEBUG_INFORMATION_FORMAT = dwarf;
-				DEVELOPMENT_TEAM = B95H74ZDY6;
+				DEVELOPMENT_TEAM = CW6GQT9SK5;
 				ENABLE_STRICT_OBJC_MSGSEND = YES;
 				ENABLE_TESTABILITY = YES;
 				ENABLE_USER_SCRIPT_SANDBOXING = YES;
@@ -361,7 +361,7 @@
 				CLANG_WARN__DUPLICATE_METHOD_MATCH = YES;
 				COPY_PHASE_STRIP = NO;
 				DEBUG_INFORMATION_FORMAT = "dwarf-with-dsym";
-				DEVELOPMENT_TEAM = B95H74ZDY6;
+				DEVELOPMENT_TEAM = CW6GQT9SK5;
 				ENABLE_NS_ASSERTIONS = NO;
 				ENABLE_STRICT_OBJC_MSGSEND = YES;
 				ENABLE_USER_SCRIPT_SANDBOXING = YES;
@@ -385,15 +385,20 @@
 			buildSettings = {
 				ASSETCATALOG_COMPILER_APPICON_NAME = AppIcon;
 				ASSETCATALOG_COMPILER_GLOBAL_ACCENT_COLOR_NAME = AccentColor;
+				ASSETCATALOG_COMPILER_INCLUDE_ALL_APPICON_ASSETS = YES;
 				CODE_SIGN_ENTITLEMENTS = Outpost/Outpost.entitlements;
+				CODE_SIGN_IDENTITY = "Apple Development";
+				"CODE_SIGN_IDENTITY[sdk=macosx*]" = "Apple Development";
 				CODE_SIGN_STYLE = Automatic;
 				CURRENT_PROJECT_VERSION = 1;
-				DEVELOPMENT_TEAM = B95H74ZDY6;
+				DEVELOPMENT_TEAM = CW6GQT9SK5;
 				ENABLE_APP_SANDBOX = YES;
 				ENABLE_HARDENED_RUNTIME = YES;
 				ENABLE_PREVIEWS = YES;
 				ENABLE_USER_SELECTED_FILES = readonly;
 				GENERATE_INFOPLIST_FILE = YES;
+				INFOPLIST_KEY_CFBundleDisplayName = Outpost;
+				INFOPLIST_KEY_LSApplicationCategoryType = "public.app-category.productivity";
 				"INFOPLIST_KEY_UIApplicationSceneManifest_Generation[sdk=iphoneos*]" = YES;
 				"INFOPLIST_KEY_UIApplicationSceneManifest_Generation[sdk=iphonesimulator*]" = YES;
 				"INFOPLIST_KEY_UIApplicationSupportsIndirectInputEvents[sdk=iphoneos*]" = YES;
@@ -408,9 +413,10 @@
 				LD_RUNPATH_SEARCH_PATHS = "@executable_path/Frameworks";
 				"LD_RUNPATH_SEARCH_PATHS[sdk=macosx*]" = "@executable_path/../Frameworks";
 				MACOSX_DEPLOYMENT_TARGET = 27.0;
-				MARKETING_VERSION = 0.0.1;
+				MARKETING_VERSION = 0.0.4;
-				PRODUCT_BUNDLE_IDENTIFIER = com.psmattas.Outpost;
+				PRODUCT_BUNDLE_IDENTIFIER = com.psmattas.OutpostApp;
 				PRODUCT_NAME = "$(TARGET_NAME)";
+				PROVISIONING_PROFILE_SPECIFIER = "";
 				REGISTER_APP_GROUPS = YES;
 				SDKROOT = auto;
 				STRING_CATALOG_GENERATE_SYMBOLS = YES;
@@ -430,15 +436,20 @@
 			buildSettings = {
 				ASSETCATALOG_COMPILER_APPICON_NAME = AppIcon;
 				ASSETCATALOG_COMPILER_GLOBAL_ACCENT_COLOR_NAME = AccentColor;
+				ASSETCATALOG_COMPILER_INCLUDE_ALL_APPICON_ASSETS = YES;
 				CODE_SIGN_ENTITLEMENTS = Outpost/Outpost.entitlements;
+				CODE_SIGN_IDENTITY = "Apple Development";
+				"CODE_SIGN_IDENTITY[sdk=macosx*]" = "Apple Development";
 				CODE_SIGN_STYLE = Automatic;
 				CURRENT_PROJECT_VERSION = 1;
-				DEVELOPMENT_TEAM = B95H74ZDY6;
+				DEVELOPMENT_TEAM = CW6GQT9SK5;
 				ENABLE_APP_SANDBOX = YES;
 				ENABLE_HARDENED_RUNTIME = YES;
 				ENABLE_PREVIEWS = YES;
 				ENABLE_USER_SELECTED_FILES = readonly;
 				GENERATE_INFOPLIST_FILE = YES;
+				INFOPLIST_KEY_CFBundleDisplayName = Outpost;
+				INFOPLIST_KEY_LSApplicationCategoryType = "public.app-category.productivity";
 				"INFOPLIST_KEY_UIApplicationSceneManifest_Generation[sdk=iphoneos*]" = YES;
 				"INFOPLIST_KEY_UIApplicationSceneManifest_Generation[sdk=iphonesimulator*]" = YES;
 				"INFOPLIST_KEY_UIApplicationSupportsIndirectInputEvents[sdk=iphoneos*]" = YES;
@@ -453,9 +464,10 @@
 				LD_RUNPATH_SEARCH_PATHS = "@executable_path/Frameworks";
 				"LD_RUNPATH_SEARCH_PATHS[sdk=macosx*]" = "@executable_path/../Frameworks";
 				MACOSX_DEPLOYMENT_TARGET = 27.0;
-				MARKETING_VERSION = 0.0.1;
+				MARKETING_VERSION = 0.0.4;
-				PRODUCT_BUNDLE_IDENTIFIER = com.psmattas.Outpost;
+				PRODUCT_BUNDLE_IDENTIFIER = com.psmattas.OutpostApp;
 				PRODUCT_NAME = "$(TARGET_NAME)";
+				PROVISIONING_PROFILE_SPECIFIER = "";
 				REGISTER_APP_GROUPS = YES;
 				SDKROOT = auto;
 				STRING_CATALOG_GENERATE_SYMBOLS = YES;
@@ -476,7 +488,7 @@
 				BUNDLE_LOADER = "$(TEST_HOST)";
 				CODE_SIGN_STYLE = Automatic;
 				CURRENT_PROJECT_VERSION = 1;
-				DEVELOPMENT_TEAM = B95H74ZDY6;
+				DEVELOPMENT_TEAM = CW6GQT9SK5;
 				GENERATE_INFOPLIST_FILE = YES;
 				IPHONEOS_DEPLOYMENT_TARGET = 27.0;
 				MACOSX_DEPLOYMENT_TARGET = 27.0;
@@ -502,7 +514,7 @@
 				BUNDLE_LOADER = "$(TEST_HOST)";
 				CODE_SIGN_STYLE = Automatic;
 				CURRENT_PROJECT_VERSION = 1;
-				DEVELOPMENT_TEAM = B95H74ZDY6;
+				DEVELOPMENT_TEAM = CW6GQT9SK5;
 				GENERATE_INFOPLIST_FILE = YES;
 				IPHONEOS_DEPLOYMENT_TARGET = 27.0;
 				MACOSX_DEPLOYMENT_TARGET = 27.0;
@@ -527,7 +539,7 @@
 			buildSettings = {
 				CODE_SIGN_STYLE = Automatic;
 				CURRENT_PROJECT_VERSION = 1;
-				DEVELOPMENT_TEAM = B95H74ZDY6;
+				DEVELOPMENT_TEAM = CW6GQT9SK5;
 				GENERATE_INFOPLIST_FILE = YES;
 				IPHONEOS_DEPLOYMENT_TARGET = 27.0;
 				MACOSX_DEPLOYMENT_TARGET = 27.0;
@@ -552,7 +564,7 @@
 			buildSettings = {
 				CODE_SIGN_STYLE = Automatic;
 				CURRENT_PROJECT_VERSION = 1;
-				DEVELOPMENT_TEAM = B95H74ZDY6;
+				DEVELOPMENT_TEAM = CW6GQT9SK5;
 				GENERATE_INFOPLIST_FILE = YES;
 				IPHONEOS_DEPLOYMENT_TARGET = 27.0;
 				MACOSX_DEPLOYMENT_TARGET = 27.0;

Outpost.xcodeproj/xcuserdata/psmattas.xcuserdatad/xcschemes/xcschememanagement.plist

@@ -1,14 +0,0 @@
-<?xml version="1.0" encoding="UTF-8"?>
-<!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
-<plist version="1.0">
-<dict>
-	<key>SchemeUserState</key>
-	<dict>
-		<key>Outpost.xcscheme_^#shared#^_</key>
-		<dict>
-			<key>orderHint</key>
-			<integer>1</integer>
-		</dict>
-	</dict>
-</dict>
-</plist>

Outpost/Assets.xcassets/AppLogo.imageset/Contents.json

@@ -0,0 +1,21 @@
+{
+  "images" : [
+    {
+      "filename" : "outpost-ios-1024.png",
+      "idiom" : "universal",
+      "scale" : "1x"
+    },
+    {
+      "idiom" : "universal",
+      "scale" : "2x"
+    },
+    {
+      "idiom" : "universal",
+      "scale" : "3x"
+    }
+  ],
+  "info" : {
+    "author" : "xcode",
+    "version" : 1
+  }
+}

Outpost/Features/About/AboutView.swift

@@ -2,25 +2,17 @@
 import AppKit
 import SwiftUI
 
-struct AboutView: View {
+/// Bare content (icon, name, version, links) with no window chrome — the
+/// macOS "About Outpost" app-menu command now opens Settings' own About
+/// section directly (no separate popup window), so this is its only caller.
+struct AboutInfoView: View {
     private let repositoryURL = URL(string: "https://git.psmattas.com/psmattas/Outpost")!
-    private let releasesURL = URL(string: "https://git.psmattas.com/psmattas/Outpost/releases")!
 
-    private var appName: String {
+    var appName: String {
         Bundle.main.object(forInfoDictionaryKey: "CFBundleName") as? String ?? "Outpost"
     }
 
-    /// Bumped alongside `MARKETING_VERSION` in the Xcode project — kept out
+    var versionString: String { OutpostVersion.fullVersionString }
-    /// of the bundle version itself since `CFBundleShortVersionString` is
-    /// expected to stay a plain dotted-numeric string, not `0.0.1-ALPHA`.
-    private let releaseStage = "ALPHA"
-
-    private var versionString: String {
-        let shortVersion = Bundle.main.object(forInfoDictionaryKey: "CFBundleShortVersionString") as? String ?? "0.0.1"
-        let buildNumber = Bundle.main.object(forInfoDictionaryKey: "CFBundleVersion") as? String ?? "1"
-        let stageSuffix = releaseStage.isEmpty ? "" : "-\(releaseStage)"
-        return "Version \(shortVersion)\(stageSuffix) (\(buildNumber))"
-    }
 
     private var copyrightYear: String {
         String(Calendar.current.component(.year, from: Date()))
@@ -51,29 +43,15 @@ struct AboutView: View {
                 .fixedSize(horizontal: false, vertical: true)
                 .frame(maxWidth: .infinity)
 
-            VStack(spacing: 10) {
             Link(destination: repositoryURL) {
                 Label("View Source on Git", systemImage: "link")
             }
             .font(.callout)
 
-                Button("Check for Updates…") {
-                    checkForUpdates()
-                }
-            }
-
             Text("© \(copyrightYear) Puranjay Savar Mattas")
                 .font(.caption2)
                 .foregroundStyle(.tertiary)
         }
-        .padding(32)
-        .frame(width: 320)
-    }
-
-    // No Sparkle-style in-app updater yet — this just opens the releases page
-    // on the self-hosted Gitea instance so the user can check/download manually.
-    private func checkForUpdates() {
-        NSWorkspace.shared.open(releasesURL)
     }
 }
 #endif

Outpost/Features/Account/AccountFooter.swift

@@ -1,5 +1,6 @@
 #if os(macOS)
 import SwiftUI
+import OutlineKit
 
 /// Uses a plain `Button` + `.popover` rather than `Menu`. A `Menu` whose label
 /// contains the avatar image reliably broke its own sizing on click (even after
@@ -7,10 +8,11 @@ import SwiftUI
 /// label rendering, which a `Button` doesn't go through.
 struct AccountFooter: View {
     @Environment(SessionStore.self) private var session
+    @Environment(AppNavigation.self) private var navigation
     @Environment(\.openURL) private var openURL
     @Environment(\.openWindow) private var openWindow
-    @Environment(\.openSettings) private var openSettings
     @AppStorage("outpost.appearance") private var appearance: AppAppearance = .system
+    @AppStorage(CachingOutlineAPIClient.offlineModeDefaultsKey) private var isOfflineModeEnabled = false
     @State private var isMenuPresented = false
     @State private var isShowingLogoutConfirmation = false
     @State private var isShowingProfile = false
@@ -93,8 +95,17 @@ struct AccountFooter: View {
             .padding(.horizontal, 6)
             .padding(.vertical, 4)
 
+            Toggle("Offline Mode", isOn: $isOfflineModeEnabled)
+                .padding(.horizontal, 6)
+                .padding(.vertical, 4)
+
             menuItem("Profile…") { isShowingProfile = true }
-            menuItem("Preferences…") { openSettings() }
+            // Deferred a tick: setting this synchronously in the same call
+            // that dismisses this popover collides two AppKit window/layer
+            // transactions in the same runloop turn (visible in the console
+            // as "Invalid attempt to open a new transaction during CA
+            // commit") — letting the popover's dismissal finish first avoids it.
+            menuItem("Settings…") { Task { @MainActor in navigation.isShowingSettings = true } }
 
             Divider()
 

Outpost/Features/Account/AvatarCropperView.swift

@@ -0,0 +1,114 @@
+#if os(macOS)
+import AppKit
+import SwiftUI
+
+/// Crop/rotate/zoom editor shown after picking a photo, before it's
+/// uploaded — pan (drag), zoom (pinch or the slider), and 90°-increment
+/// rotate, all inside a circular mask matching how the avatar actually
+/// renders everywhere else in the app.
+///
+/// The on-screen preview and the final exported image are built from the
+/// exact same view composition (`avatarContent`), just instantiated once
+/// for display and once inside an `ImageRenderer` — that's deliberate:
+/// hand-deriving a separate set of crop-math for a higher-resolution
+/// render would risk it silently disagreeing with what the user actually
+/// saw and confirmed, and there's no way to visually verify that
+/// agreement without running the app. Reusing the identical view tree
+/// makes the export WYSIWYG by construction instead of by careful math.
+struct AvatarCropperView: View {
+    let sourceImage: NSImage
+    let onConfirm: (Data) -> Void
+    let onCancel: () -> Void
+
+    @State private var scale: CGFloat = 1
+    @State private var offset: CGSize = .zero
+    @State private var rotationDegrees: Double = 0
+    @GestureState private var dragTranslation: CGSize = .zero
+
+    /// Used for both the live preview and the exported image — see the
+    /// type-level doc comment for why that's the same size, not two.
+    private let diameter: CGFloat = 320
+
+    var body: some View {
+        VStack(spacing: 20) {
+            Text("Edit Photo")
+                .font(.headline)
+
+            ZStack {
+                avatarContent
+                    .clipShape(Circle())
+                Circle()
+                    .strokeBorder(Color.primary.opacity(0.15), lineWidth: 1)
+            }
+            .frame(width: diameter, height: diameter)
+            .contentShape(Circle())
+            .gesture(
+                DragGesture()
+                    .updating($dragTranslation) { value, state, _ in state = value.translation }
+                    .onEnded { value in
+                        offset.width += value.translation.width
+                        offset.height += value.translation.height
+                    }
+            )
+
+            HStack(spacing: 16) {
+                Button {
+                    withAnimation(.easeInOut(duration: 0.2)) { rotationDegrees -= 90 }
+                } label: {
+                    Image(systemName: "rotate.left")
+                }
+                .help("Rotate left")
+
+                Slider(value: $scale, in: 1...4)
+                    .frame(width: 140)
+
+                Button {
+                    withAnimation(.easeInOut(duration: 0.2)) { rotationDegrees += 90 }
+                } label: {
+                    Image(systemName: "rotate.right")
+                }
+                .help("Rotate right")
+            }
+
+            HStack {
+                Button("Cancel", role: .cancel, action: onCancel)
+                Spacer()
+                Button("Use Photo") {
+                    if let data = renderFinalImage() {
+                        onConfirm(data)
+                    }
+                }
+                .buttonStyle(.borderedProminent)
+            }
+        }
+        .padding(24)
+        .frame(width: 360)
+    }
+
+    /// Aspect-fills `sourceImage` into a `diameter`×`diameter` square, then
+    /// applies the user's pan/zoom/rotation on top — identical between the
+    /// live preview and the final render (see the type-level doc comment).
+    private var avatarContent: some View {
+        Image(nsImage: sourceImage)
+            .resizable()
+            .aspectRatio(contentMode: .fill)
+            .frame(width: diameter, height: diameter)
+            .scaleEffect(scale)
+            .rotationEffect(.degrees(rotationDegrees))
+            .offset(x: offset.width + dragTranslation.width, y: offset.height + dragTranslation.height)
+            .frame(width: diameter, height: diameter)
+            .clipped()
+    }
+
+    @MainActor
+    private func renderFinalImage() -> Data? {
+        let content = avatarContent
+            .clipShape(Circle())
+            .frame(width: diameter, height: diameter)
+        let renderer = ImageRenderer(content: content)
+        renderer.scale = 2 // @2x so it isn't a blurry 320px avatar on Retina displays
+        guard let nsImage = renderer.nsImage else { return nil }
+        return nsImage.jpegData(compressionQuality: 0.9)
+    }
+}
+#endif

Outpost/Features/Account/PreferencesView.swift

@@ -1,40 +0,0 @@
-#if os(macOS)
-import SwiftUI
-
-struct PreferencesView: View {
-    @Environment(SessionStore.self) private var session
-    @AppStorage("outpost.appearance") private var appearance: AppAppearance = .system
-    @State private var isShowingLogoutConfirmation = false
-
-    var body: some View {
-        Form {
-            Section("Appearance") {
-                Picker("Appearance", selection: $appearance) {
-                    ForEach(AppAppearance.allCases) { option in
-                        Text(option.label).tag(option)
-                    }
-                }
-                .pickerStyle(.segmented)
-                .labelsHidden()
-            }
-
-            Section("Account") {
-                LabeledContent("Signed in as", value: session.userName ?? "—")
-                if let email = session.userEmail {
-                    LabeledContent("Email", value: email)
-                }
-                if let teamName = session.teamName {
-                    LabeledContent("Workspace", value: teamName)
-                }
-
-                Button("Log Out…", role: .destructive) {
-                    isShowingLogoutConfirmation = true
-                }
-            }
-        }
-        .formStyle(.grouped)
-        .frame(width: 380, height: 300)
-        .logoutConfirmationDialog(isPresented: $isShowingLogoutConfirmation, session: session)
-    }
-}
-#endif

Outpost/Features/Account/SettingsSidebarList.swift

@@ -0,0 +1,115 @@
+#if os(macOS)
+import SwiftUI
+import OutlineKit
+
+/// Swapped into the real sidebar's content slot (search field, collections
+/// tree, account footer) while Settings is open — same sidebar, different
+/// content, rather than a separate mini sidebar nested inside a page. "Done"
+/// clears `AppNavigation.isShowingSettings`, which puts the collections tree
+/// back.
+///
+/// Grouped by `SettingsCategory` — `general` (ours) sits under an "Outpost"
+/// header at the top, then Outline's own Account/Workspace groups, matching
+/// the settings page structure of the Outline web app. Outline's own server
+/// version has no dedicated section (there used to be an Integrations &
+/// Installation category for just that) — it's cheap enough to show
+/// unconditionally in the footer here instead, alongside Outpost's own
+/// version.
+struct SettingsSidebarList: View {
+    @Binding var selection: SettingsSection?
+    let onDone: () -> Void
+
+    @Environment(SessionStore.self) private var session
+    @AppStorage(CachingOutlineAPIClient.offlineModeDefaultsKey) private var isOfflineModeEnabled = false
+    @State private var outlineVersion: String?
+
+    /// Mirrors `SettingsView`'s own check — a real dropped connection or
+    /// the manual Offline Mode toggle both mean there's no server to ask.
+    private var isEffectivelyOnline: Bool {
+        session.networkMonitor.isOnline && !isOfflineModeEnabled
+    }
+
+    var body: some View {
+        VStack(spacing: 0) {
+            HStack {
+                Text("Settings")
+                    .font(.headline)
+                Spacer()
+            }
+            .padding(.horizontal, 16)
+            .padding(.vertical, 12)
+
+            Divider()
+
+            List(selection: $selection) {
+                ForEach(SettingsCategory.allCases) { category in
+                    let sections = SettingsSection.allCases.filter { $0.category == category }
+                    Section {
+                        ForEach(sections) { section in
+                            Label(section.title, systemImage: section.icon)
+                                .tag(section)
+                        }
+                    } header: {
+                        if let title = category.title {
+                            HStack(spacing: 6) {
+                                Text(title)
+                                // Not hardcoded to `.workspace` specifically —
+                                // stays correct on its own as sections get
+                                // built, only shows while every section in
+                                // the category is still `!isImplemented`.
+                                if sections.allSatisfy({ !$0.isImplemented }) {
+                                    Text("Coming Soon")
+                                        .font(.system(size: 9, weight: .semibold))
+                                        .foregroundStyle(.secondary)
+                                        .padding(.horizontal, 6)
+                                        .padding(.vertical, 2)
+                                        .background(.secondary.opacity(0.15), in: Capsule())
+                                }
+                            }
+                        }
+                    }
+                }
+            }
+            .listStyle(.sidebar)
+
+            Divider()
+
+            versionFooter
+
+            Divider()
+
+            Button("Done", action: onDone)
+                .keyboardShortcut(.cancelAction)
+                .buttonStyle(.borderedProminent)
+                .frame(maxWidth: .infinity)
+                .padding(12)
+        }
+        // Keyed to connectivity, not a one-shot `.task {}` — reconnecting
+        // (or turning the manual Offline Mode toggle back off) re-fires
+        // this automatically instead of leaving the footer stuck on
+        // whatever it last knew, or blank, until Settings is reopened.
+        .task(id: isEffectivelyOnline) { await refreshOutlineVersion() }
+    }
+
+    private var versionFooter: some View {
+        VStack(alignment: .leading, spacing: 2) {
+            Text("Outpost \(OutpostVersion.displayString)")
+            if let outlineVersion {
+                Text("Outline \(outlineVersion)")
+            } else if !isEffectivelyOnline {
+                Text("Outline — offline")
+            }
+        }
+        .font(.caption2)
+        .foregroundStyle(.tertiary)
+        .frame(maxWidth: .infinity, alignment: .leading)
+        .padding(.horizontal, 16)
+        .padding(.vertical, 8)
+    }
+
+    private func refreshOutlineVersion() async {
+        guard isEffectivelyOnline, let apiClient = session.apiClient else { return }
+        outlineVersion = try? await apiClient.installationInfo().version
+    }
+}
+#endif

Outpost/Features/Auth/AuthHeaderView.swift

@@ -3,21 +3,17 @@ import SwiftUI
 struct AuthHeaderView: View {
     var body: some View {
         VStack(spacing: 12) {
-            ZStack {
+            // A plain Image Set, not the AppIcon *app icon* asset — App Icon
-                Circle()
+            // sets aren't reliably resolvable through Image(_:)/UIImage
-                    .fill(
+            // (named:) at runtime (confirmed live: showed nothing). This is
-                        LinearGradient(
+            // the same source artwork (outpost-ios-1024.png) duplicated
-                            colors: [Color.accentColor, Color.accentColor.opacity(0.6)],
+            // into a normal image set so SwiftUI can actually load it.
-                            startPoint: .topLeading,
+            Image("AppLogo")
-                            endPoint: .bottomTrailing
+                .resizable()
-                        )
+                .scaledToFit()
-                    )
+                .frame(width: 72, height: 72)
-                    .frame(width: 64, height: 64)
+                .clipShape(RoundedRectangle(cornerRadius: 72 * 0.2237, style: .continuous))
-                Image(systemName: "text.book.closed.fill")
+                .shadow(color: .black.opacity(0.25), radius: 12, y: 6)
-                    .font(.system(size: 26, weight: .semibold))
-                    .foregroundStyle(.white)
-            }
-            .shadow(color: Color.accentColor.opacity(0.35), radius: 12, y: 6)
 
             VStack(spacing: 4) {
                 Text("Welcome to Outpost")

Outpost/Features/Collections/CollectionDocumentsOutline.swift

@@ -9,14 +9,27 @@ import OutlineKit
 /// client-side rather than `collections.documents`.
 struct CollectionDocumentsOutline: View {
     let apiClient: OutlineAPIClient
+    let collection: OutlineCollection
     @State private var viewModel: DocumentsViewModel
     let sortOption: SidebarSortOption
     let refreshToken: Int
+    /// Bumped from `ContentView_macOS` whenever a document is created from
+    /// somewhere that has no direct handle on this row — the reader's
+    /// toolbar "New Document" button and Home's, specifically. Those can't
+    /// call `onDocumentsChanged()` the way a same-row sheet does, since they
+    /// don't know which (if any) sidebar row corresponds to where the new
+    /// document landed, so every expanded row just reloads itself.
+    let externalRefreshToken: Int
     let selectedDocumentID: String?
     /// Full chain from root to the clicked document (inclusive) — lets the
     /// toolbar render the real hierarchy instead of just the leaf title.
     let onSelectDocument: ([OutlineDocument]) -> Void
 
+    /// Loaded once per collection (`pins.list` is collection-scoped) rather
+    /// than per-row — a per-row `pins.list`/lookup would be an N+1 call for
+    /// every document in the tree.
+    @State private var pinsByDocumentID: [String: OutlinePin] = [:]
+
     private var tree: [DocumentNode] {
         buildDocumentTree(from: viewModel.documents, sortedBy: sortOption)
     }
@@ -26,13 +39,16 @@ struct CollectionDocumentsOutline: View {
         collection: OutlineCollection,
         sortOption: SidebarSortOption,
         refreshToken: Int,
+        externalRefreshToken: Int,
         selectedDocumentID: String?,
         onSelectDocument: @escaping ([OutlineDocument]) -> Void
     ) {
         self.apiClient = apiClient
+        self.collection = collection
         _viewModel = State(initialValue: DocumentsViewModel(apiClient: apiClient, collection: collection))
         self.sortOption = sortOption
         self.refreshToken = refreshToken
+        self.externalRefreshToken = externalRefreshToken
         self.selectedDocumentID = selectedDocumentID
         self.onSelectDocument = onSelectDocument
     }
@@ -56,13 +72,26 @@ struct CollectionDocumentsOutline: View {
                         depth: 0,
                         ancestors: [],
                         selectedDocumentID: selectedDocumentID,
+                        pinsByDocumentID: pinsByDocumentID,
                         onSelectDocument: onSelectDocument,
-                        onDocumentsChanged: { await viewModel.load() }
+                        onDocumentsChanged: { await viewModel.load() },
+                        onPinsChanged: { await loadPins() }
                     )
                 }
             }
         }
-        .task(id: refreshToken) { await viewModel.load() }
+        // Combined into one identity rather than two separate `.task(id:)`
+        // modifiers — each of those fires once unconditionally on first
+        // appear, so two of them would double the initial load.
+        .task(id: "\(refreshToken)-\(externalRefreshToken)") {
+            await viewModel.load()
+            await loadPins()
+        }
+    }
+
+    private func loadPins() async {
+        guard let pins = try? await apiClient.listPins(ListPinsRequest(collectionId: collection.id)) else { return }
+        pinsByDocumentID = Dictionary(uniqueKeysWithValues: pins.map { ($0.documentId, $0) })
     }
 }
 
@@ -81,8 +110,10 @@ private struct DocumentNodeRow: View {
     /// Chain from root down to (not including) this node.
     let ancestors: [OutlineDocument]
     let selectedDocumentID: String?
+    let pinsByDocumentID: [String: OutlinePin]
     let onSelectDocument: ([OutlineDocument]) -> Void
     let onDocumentsChanged: () async -> Void
+    let onPinsChanged: () async -> Void
 
     @State private var isExpanded = false
 
@@ -96,6 +127,7 @@ private struct DocumentNodeRow: View {
     @State private var isShowingInsightsSheet = false
     @State private var isShowingPresentSheet = false
     @State private var isShowingSearchSheet = false
+    @State private var isShowingNewDocumentSheet = false
     @State private var actionErrorMessage: String?
 
     private var isSelected: Bool {
@@ -172,8 +204,10 @@ private struct DocumentNodeRow: View {
                         depth: depth + 1,
                         ancestors: ancestors + [node.document],
                         selectedDocumentID: selectedDocumentID,
+                        pinsByDocumentID: pinsByDocumentID,
                         onSelectDocument: onSelectDocument,
-                        onDocumentsChanged: onDocumentsChanged
+                        onDocumentsChanged: onDocumentsChanged,
+                        onPinsChanged: onPinsChanged
                     )
                 }
             }
@@ -252,6 +286,11 @@ private struct DocumentNodeRow: View {
         .sheet(isPresented: $isShowingSearchSheet) {
             DocumentSearchSheet(apiClient: apiClient, document: node.document)
         }
+        .sheet(isPresented: $isShowingNewDocumentSheet) {
+            NewDocumentSheet(apiClient: apiClient, initialParentDocument: node.document) { _ in
+                Task { await onDocumentsChanged() }
+            }
+        }
     }
 
     @ViewBuilder
@@ -259,7 +298,11 @@ private struct DocumentNodeRow: View {
         Button(starStore.isStarred(documentId: node.document.id) ? "Unstar" : "Star") {
             Task { await star() }
         }
-        // No `subscriptions.*` endpoint in the API — nothing to back this with.
+        // subscriptions.* does exist and works (confirmed against a live
+        // server via the reader's menu) — not shown here because
+        // subscriptions.list is per-document, so reflecting accurate
+        // per-row state for every document in the tree would mean an N+1
+        // call storm. Use the reader's ⋯ menu instead.
         Button("Unsubscribe") {}
             .disabled(true)
 
@@ -273,8 +316,9 @@ private struct DocumentNodeRow: View {
             renameText = node.document.title
             isShowingRenameAlert = true
         }
-        // Sharing/membership management is its own subsystem, not a one-off
+        // DocumentShareSheet now has a real "People with access" section —
-        // action — deferred rather than half-built here.
+        // this row just doesn't have a sheet wired up to present it yet
+        // (only the reader toolbar does). Use the reader's ⋯ menu instead.
         Button("Permissions…") {}
             .disabled(true)
 
@@ -303,11 +347,13 @@ private struct DocumentNodeRow: View {
         Button("Import Document…") {}
             .disabled(true)
         Button("New Document") {
-            Task { await createChildDocument() }
+            isShowingNewDocumentSheet = true
+        }
+        // Scoped to this collection (`collection.id`) — "Pin to Collection",
+        // distinct from the reader toolbar's "Pin to Home" (collectionId: nil).
+        Button(pinsByDocumentID[node.document.id] != nil ? "Unpin from Collection" : "Pin to Collection") {
+            Task { await togglePin() }
         }
-        // No `pins.*` endpoint in the API — nothing to back this with.
-        Button("Pin") {}
-            .disabled(true)
 
         Divider()
 
@@ -351,6 +397,19 @@ private struct DocumentNodeRow: View {
         }
     }
 
+    private func togglePin() async {
+        do {
+            if let pin = pinsByDocumentID[node.document.id] {
+                try await apiClient.deletePin(id: pin.id)
+            } else {
+                _ = try await apiClient.createPin(CreatePinRequest(documentId: node.document.id, collectionId: node.document.collectionId))
+            }
+            await onPinsChanged()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't update pin state.")
+        }
+    }
+
     private func rename() async {
         do {
             _ = try await apiClient.updateDocument(UpdateDocumentRequest(id: node.document.id, title: renameText))
@@ -395,26 +454,6 @@ private struct DocumentNodeRow: View {
         }
     }
 
-    private func createChildDocument() async {
-        guard let collectionId = node.document.collectionId else {
-            actionErrorMessage = "This document isn't in a collection."
-            return
-        }
-        do {
-            _ = try await apiClient.createDocument(
-                CreateDocumentRequest(
-                    title: "Untitled",
-                    text: "",
-                    collectionId: collectionId,
-                    parentDocumentId: node.document.id
-                )
-            )
-            await onDocumentsChanged()
-        } catch {
-            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't create a new document.")
-        }
-    }
-
     private func delete() async {
         do {
             try await apiClient.deleteDocument(DeleteDocumentRequest(id: node.document.id))

Outpost/Features/Collections/CollectionRowView.swift

@@ -10,7 +10,7 @@ struct CollectionRowView: View {
         } icon: {
             if let emoji = collection.emojiIcon {
                 Text(emoji)
-            } else if let symbolName = collection.icon.flatMap(OutlineIconMapping.sfSymbolName) {
+            } else if let symbolName = collection.icon.flatMap({ OutlineIconMapping.sfSymbolName(for: $0) }) {
                 Image(systemName: symbolName)
                     .foregroundStyle(tintColor)
             } else {

Outpost/Features/Collections/CollectionTreeRow.swift

@@ -11,6 +11,8 @@ struct CollectionTreeRow: View {
     let isExpanded: Bool
     let isSelected: Bool
     let selectedDocumentID: String?
+    /// See the identical parameter on `CollectionDocumentsOutline`.
+    let externalRefreshToken: Int
     let onToggle: () -> Void
     let onSelectDocument: ([OutlineDocument]) -> Void
     let onSearchInCollection: (OutlineCollection) -> Void
@@ -22,6 +24,7 @@ struct CollectionTreeRow: View {
     @State private var isShowingRenameAlert = false
     @State private var renameText = ""
     @State private var isShowingDeleteConfirmation = false
+    @State private var isShowingNewDocumentSheet = false
     @State private var actionErrorMessage: String?
 
     var body: some View {
@@ -62,6 +65,7 @@ struct CollectionTreeRow: View {
                     collection: collection,
                     sortOption: sortOption,
                     refreshToken: documentsRefreshToken,
+                    externalRefreshToken: externalRefreshToken,
                     selectedDocumentID: selectedDocumentID,
                     onSelectDocument: onSelectDocument
                 )
@@ -92,6 +96,12 @@ struct CollectionTreeRow: View {
         } message: {
             Text(actionErrorMessage ?? "")
         }
+        .sheet(isPresented: $isShowingNewDocumentSheet) {
+            NewDocumentSheet(apiClient: apiClient, initialCollectionID: collection.id) { _ in
+                documentsRefreshToken += 1
+                Task { await onCollectionsChanged() }
+            }
+        }
     }
 
     @ViewBuilder
@@ -103,7 +113,7 @@ struct CollectionTreeRow: View {
         Divider()
 
         Button("New Document") {
-            Task { await createDocument() }
+            isShowingNewDocumentSheet = true
         }
 
         Divider()
@@ -148,18 +158,6 @@ struct CollectionTreeRow: View {
         }
     }
 
-    private func createDocument() async {
-        do {
-            _ = try await apiClient.createDocument(
-                CreateDocumentRequest(title: "Untitled", text: "", collectionId: collection.id)
-            )
-            documentsRefreshToken += 1
-            await onCollectionsChanged()
-        } catch {
-            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't create a new document.")
-        }
-    }
-
     private func rename() async {
         do {
             _ = try await apiClient.updateCollection(UpdateCollectionRequest(id: collection.id, name: renameText))

Outpost/Features/Collections/CollectionsTreeView.swift

@@ -7,6 +7,12 @@ struct CollectionsTreeView: View {
     @Binding private var selectedCollection: OutlineCollection?
     let selectedDocumentID: String?
     @State private var expandedCollectionIDs: Set<String> = []
+    /// Bumped from `ContentView_macOS` whenever a document is created
+    /// somewhere with no direct handle on the sidebar row it belongs
+    /// under — see the identical parameter on `CollectionDocumentsOutline`.
+    let externalRefreshToken: Int
+    let isShowingHome: Bool
+    let onSelectHome: () -> Void
     let onSelectDocument: (OutlineCollection, [OutlineDocument]) -> Void
     let onSearchInCollection: (OutlineCollection) -> Void
 
@@ -14,12 +20,18 @@ struct CollectionsTreeView: View {
         apiClient: OutlineAPIClient,
         selectedCollection: Binding<OutlineCollection?>,
         selectedDocumentID: String?,
+        externalRefreshToken: Int,
+        isShowingHome: Bool,
+        onSelectHome: @escaping () -> Void,
         onSelectDocument: @escaping (OutlineCollection, [OutlineDocument]) -> Void,
         onSearchInCollection: @escaping (OutlineCollection) -> Void
     ) {
         _viewModel = State(initialValue: CollectionsViewModel(apiClient: apiClient))
         _selectedCollection = selectedCollection
         self.selectedDocumentID = selectedDocumentID
+        self.externalRefreshToken = externalRefreshToken
+        self.isShowingHome = isShowingHome
+        self.onSelectHome = onSelectHome
         self.onSelectDocument = onSelectDocument
         self.onSearchInCollection = onSearchInCollection
     }
@@ -31,6 +43,7 @@ struct CollectionsTreeView: View {
                     Task { await viewModel.load() }
                 }
             }
+            homeRow
             content
         }
         .task {
@@ -42,6 +55,32 @@ struct CollectionsTreeView: View {
         }
     }
 
+    /// Pinned above the collections list, not inside the scroll region —
+    /// Home isn't a collection, so it doesn't belong in `viewModel.collections`
+    /// or compete with them for scroll space.
+    private var homeRow: some View {
+        Button(action: onSelectHome) {
+            HStack(spacing: 6) {
+                Image(systemName: "house.fill")
+                    .font(.callout)
+                    .foregroundStyle(.secondary)
+                Text("Home")
+                    .font(.body)
+                Spacer(minLength: 0)
+            }
+            .padding(.vertical, 4)
+            .padding(.horizontal, 6)
+            .contentShape(Rectangle())
+            .background(
+                isShowingHome ? Color.accentColor.opacity(0.15) : Color.clear,
+                in: RoundedRectangle(cornerRadius: 6)
+            )
+        }
+        .buttonStyle(.plain)
+        .padding(.horizontal, 8)
+        .padding(.top, 4)
+    }
+
     @ViewBuilder
     private var content: some View {
         Group {
@@ -81,6 +120,7 @@ struct CollectionsTreeView: View {
                                 isExpanded: expandedCollectionIDs.contains(collection.id),
                                 isSelected: selectedCollection?.id == collection.id,
                                 selectedDocumentID: selectedDocumentID,
+                                externalRefreshToken: externalRefreshToken,
                                 onToggle: { toggle(collection) },
                                 onSelectDocument: { chain in onSelectDocument(collection, chain) },
                                 onSearchInCollection: onSearchInCollection,
@@ -95,13 +135,6 @@ struct CollectionsTreeView: View {
         }
         .task {
             await viewModel.load()
-            // Stand-in for Outline's own configured "Start view" — we don't have
-            // a confirmed schema for `team.preferences` to read the actual
-            // setting, so this defaults to the first collection instead of
-            // landing on an empty "No Collection Selected" placeholder.
-            if selectedCollection == nil, let first = viewModel.collections.first {
-                selectedCollection = first
-            }
         }
         // A document opened from outside the sidebar (detail pane's list,
         // global search) wouldn't otherwise expand its collection here, so

Outpost/Features/Collections/ContentView_macOS.swift

@@ -4,6 +4,12 @@ import OutlineKit
 
 struct ContentView_macOS: View {
     @Environment(SessionStore.self) private var session
+    @Environment(AppNavigation.self) private var navigation
+    @AppStorage(CachingOutlineAPIClient.offlineModeDefaultsKey) private var isOfflineModeEnabled = false
+    /// The landing state — no collection selected yet is what Home actually
+    /// means, so this starts `true` rather than auto-selecting the first
+    /// collection the way this used to work.
+    @State private var isShowingHome = true
     @State private var selectedCollection: OutlineCollection?
     /// The real navigation stack, root to leaf — also the source of truth for
     /// the toolbar breadcrumb, so the two can't drift out of sync.
@@ -12,16 +18,83 @@ struct ContentView_macOS: View {
     @State private var contextualSearchQuery = ""
     @State private var isContextualSearchExpanded = false
     @FocusState private var isContextualSearchFocused: Bool
+    /// Bumped whenever a document is created from somewhere with no direct
+    /// handle on the sidebar row it belongs under (the reader toolbar's and
+    /// Home's "New Document" buttons) — every expanded sidebar row reloads
+    /// itself in response. See `CollectionDocumentsOutline.externalRefreshToken`.
+    @State private var documentsChangedToken = 0
 
     private var trimmedGlobalQuery: String {
         globalSearchQuery.trimmingCharacters(in: .whitespacesAndNewlines)
     }
 
+    /// `@Environment(AppNavigation.self)` doesn't hand out `$`-bindings on its
+    /// own (that's `@Bindable`'s job, and introducing one in `body` would
+    /// mean restructuring it away from a single implicit-return expression)
+    /// — a manually-built `Binding` over the same reference is simpler here.
+    private var selectedSettingsSectionBinding: Binding<SettingsSection?> {
+        Binding(
+            get: { navigation.selectedSettingsSection },
+            set: { navigation.selectedSettingsSection = $0 }
+        )
+    }
+
     var body: some View {
+        // A totally separate top-level branch, not content swapped inside
+        // one persistent `NavigationSplitView` — that was tried first (an
+        // `if/else` inside a single split view, then an explicit `.id()` on
+        // just the detail pane) and neither reliably replaced the detail
+        // pane's content on macOS: `NavigationSplitView` bridges to
+        // `NSSplitViewController`, and swapping a `NavigationStack` with
+        // real push history for a plain view inside one persisting instance
+        // doesn't propagate the way plain SwiftUI identity rules would
+        // suggest. A different `if` branch is a genuinely different view
+        // hierarchy, so there's no existing split view instance for AppKit
+        // to get confused about reusing.
+        if navigation.isShowingSettings {
+            settingsContent
+        } else {
+            mainContent
+        }
+    }
+
+    private var settingsContent: some View {
+        NavigationSplitView {
+            SettingsSidebarList(
+                selection: selectedSettingsSectionBinding,
+                onDone: { navigation.isShowingSettings = false }
+            )
+            .navigationSplitViewColumnWidth(min: 220, ideal: 260)
+        } detail: {
+            SettingsView(section: navigation.selectedSettingsSection ?? .appearance)
+        }
+        .navigationTitle("")
+        .toolbar {
+            ToolbarItem(placement: .navigation) {
+                HStack(spacing: 6) {
+                    Image(systemName: "gearshape.fill")
+                    Text("Settings")
+                }
+                .font(.headline)
+                .padding(.horizontal, 10)
+                .padding(.vertical, 4)
+                .background(.fill.tertiary, in: Capsule())
+            }
+        }
+    }
+
+    private var mainContent: some View {
         NavigationSplitView {
             VStack(spacing: 0) {
                 SidebarSearchField(text: $globalSearchQuery)
                 Divider()
+                if isOfflineModeEnabled {
+                    OfflineBanner(isManual: true)
+                    Divider()
+                } else if !session.networkMonitor.isOnline {
+                    OfflineConnectionPromptBanner(onEnableOfflineMode: { isOfflineModeEnabled = true })
+                    Divider()
+                }
                 sidebar
                 AccountFooter()
             }
@@ -43,18 +116,49 @@ struct ContentView_macOS: View {
             // mutually exclusive: whenever a document's pushed (back button
             // visible), this shows the document hierarchy instead of falling
             // back to the workspace badge.
+            ToolbarItem(placement: .navigation) {
+                Button {
+                    goHome()
+                } label: {
+                    Image(systemName: "house")
+                }
+                .help("Home")
+            }
             ToolbarItem(placement: .navigation) {
                 leadingToolbarContent
             }
             // Custom instead of `.searchable`: that modifier always renders a
             // full-width field, but this is meant to sit alongside the other
             // per-document toolbar buttons as a plain icon that only expands
-            // into a field once clicked.
+            // into a field once clicked. Hidden on the Home landing page
+            // itself — `contextualSearchQuery` is only ever read by
+            // `CollectionOverviewView`, so on Home it was a dead end: a
+            // user could click it, type, and nothing would happen. The
+            // sidebar's global search already covers "search everything."
+            if !(isShowingHome && documentPath.isEmpty) {
                 ToolbarItem(placement: .primaryAction) {
                     contextualSearchField
                 }
             }
         }
+        // Any explicit collection pick — sidebar click, "Search in
+        // Collection" — means the user has navigated away from Home.
+        .onChange(of: selectedCollection) { _, newValue in
+            if newValue != nil {
+                isShowingHome = false
+            }
+        }
+    }
+
+    private func goHome() {
+        globalSearchQuery = ""
+        contextualSearchQuery = ""
+        isContextualSearchExpanded = false
+        selectedCollection = nil
+        isShowingHome = true
+        navigation.isShowingSettings = false
+        replaceDocumentPath(with: [])
+    }
 
     @ViewBuilder
     private var contextualSearchField: some View {
@@ -106,12 +210,19 @@ struct ContentView_macOS: View {
                     Image(systemName: "magnifyingglass")
                     Text("Search")
                 }
-            } else if !documentPath.isEmpty, let selectedCollection {
+            } else if !documentPath.isEmpty {
-                // Collection → every ancestor (icon only) → current document
+                // Origin (collection, or Home if opened from there) → every
-                // (icon + full title) — ancestors stay icon-only so a deep
+                // ancestor (icon only) → current document (icon + full
-                // chain doesn't blow out the toolbar width.
+                // title) — ancestors stay icon-only so a deep chain doesn't
+                // blow out the toolbar width. Checked before `isShowingHome`
+                // since opening a document from Home still leaves that flag
+                // set — the pushed document should win either way.
                 HStack(spacing: 6) {
+                    if let selectedCollection {
                         CollectionRowView(collection: selectedCollection)
+                    } else {
+                        Image(systemName: "house.fill")
+                    }
 
                     ForEach(Array(documentPath.enumerated()), id: \.element.id) { index, document in
                         Image(systemName: "chevron.right")
@@ -130,6 +241,11 @@ struct ContentView_macOS: View {
                         }
                     }
                 }
+            } else if isShowingHome {
+                HStack(spacing: 6) {
+                    Image(systemName: "house.fill")
+                    Text("Home")
+                }
             } else if let selectedCollection {
                 CollectionRowView(collection: selectedCollection)
             } else {
@@ -153,6 +269,9 @@ struct ContentView_macOS: View {
                 apiClient: apiClient,
                 selectedCollection: $selectedCollection,
                 selectedDocumentID: documentPath.last?.id,
+                externalRefreshToken: documentsChangedToken,
+                isShowingHome: isShowingHome,
+                onSelectHome: goHome,
                 onSelectDocument: selectDocumentChain,
                 onSearchInCollection: searchInCollection
             )
@@ -205,6 +324,8 @@ struct ContentView_macOS: View {
                 Group {
                     if !trimmedGlobalQuery.isEmpty {
                         GlobalSearchResultsView(apiClient: apiClient, query: trimmedGlobalQuery, onOpenDocument: openDocument)
+                    } else if isShowingHome {
+                        HomeView(apiClient: apiClient, onOpenDocument: openDocument, onDocumentCreated: { documentsChangedToken += 1 })
                     } else if let selectedCollection {
                         CollectionOverviewView(
                             apiClient: apiClient,
@@ -229,11 +350,12 @@ struct ContentView_macOS: View {
                             if !documentPath.isEmpty {
                                 documentPath.removeLast()
                             }
-                        }
+                        },
+                        onDocumentCreated: { documentsChangedToken += 1 }
                     )
                 }
             }
-            .id(trimmedGlobalQuery.isEmpty ? (selectedCollection?.id ?? "none") : "search")
+            .id(trimmedGlobalQuery.isEmpty ? (isShowingHome ? "home" : (selectedCollection?.id ?? "none")) : "search")
         } else {
             ContentUnavailableView("Not Signed In", systemImage: "person.crop.circle.badge.exclamationmark")
         }

Outpost/Features/Collections/DocumentReaderView.swift

@@ -12,6 +12,7 @@ import OutlineKit
 struct DocumentReaderView: View {
     @Environment(SessionStore.self) private var session
     @Environment(StarStore.self) private var starStore
+    @AppStorage(CachingOutlineAPIClient.offlineModeDefaultsKey) private var isOfflineModeEnabled = false
 
     @State private var viewModel: DocumentReaderViewModel
     let apiClient: OutlineAPIClient
@@ -23,6 +24,11 @@ struct DocumentReaderView: View {
     /// longer visible in the collection it was opened from, so the reader
     /// pops itself off the navigation stack.
     let onDeleted: () -> Void
+    /// The reader's own "New Document" toolbar button has no direct handle
+    /// on the sidebar row it belongs under — this tells the sidebar a
+    /// document exists now so it can pick it up. See
+    /// `CollectionDocumentsOutline.externalRefreshToken`.
+    let onDocumentCreated: () -> Void
 
     @State private var isShowingUnpublishConfirmation = false
     @State private var isShowingArchiveConfirmation = false
@@ -33,19 +39,31 @@ struct DocumentReaderView: View {
     @State private var isShowingPresentSheet = false
     @State private var isShowingSearchSheet = false
     @State private var isShowingShareSheet = false
+    @State private var isShowingNewDocumentSheet = false
     @State private var actionErrorMessage: String?
 
     init(
         apiClient: OutlineAPIClient,
         document: OutlineDocument,
         onOpenChild: @escaping (OutlineDocument) -> Void,
-        onDeleted: @escaping () -> Void
+        onDeleted: @escaping () -> Void,
+        onDocumentCreated: @escaping () -> Void
     ) {
         self.apiClient = apiClient
         self.document = document
         _viewModel = State(initialValue: DocumentReaderViewModel(apiClient: apiClient, document: document))
         self.onOpenChild = onOpenChild
         self.onDeleted = onDeleted
+        self.onDocumentCreated = onDocumentCreated
+    }
+
+    /// New Document, editing, pin/star/subscribe, and Full Width all queue
+    /// and sync later (see `CachingOutlineAPIClient`) — everything else here
+    /// (sharing, permissions, move/archive/delete/duplicate/templatize,
+    /// history, insights, export) hits the server directly with no offline
+    /// path, so it's disabled rather than left to fail confusingly on tap.
+    private var isEffectivelyOnline: Bool {
+        session.networkMonitor.isOnline && !isOfflineModeEnabled
     }
 
     var body: some View {
@@ -74,6 +92,7 @@ struct DocumentReaderView: View {
                     NativeTextViewWrapper(
                         text: $viewModel.text,
                         configuration: .init(heightBehavior: .fitsContent),
+                        documentId: viewModel.documentId,
                         isEditable: viewModel.isEditing
                     )
 
@@ -102,7 +121,11 @@ struct DocumentReaderView: View {
                 } label: {
                     Image(systemName: "square.and.arrow.up")
                 }
-                .help("Share")
+                .help(isEffectivelyOnline ? "Share" : "Sharing needs an internet connection")
+                .disabled(!isEffectivelyOnline)
+                .popover(isPresented: $isShowingShareSheet, arrowEdge: .bottom) {
+                    DocumentShareSheet(apiClient: apiClient, documentId: viewModel.documentId)
+                }
 
                 Button {
                     Task { await viewModel.toggleEditing() }
@@ -116,7 +139,7 @@ struct DocumentReaderView: View {
                 .disabled(viewModel.isSaving)
 
                 Button {
-                    Task { await createChildDocument() }
+                    isShowingNewDocumentSheet = true
                 } label: {
                     Image(systemName: "doc.badge.plus")
                 }
@@ -127,12 +150,22 @@ struct DocumentReaderView: View {
                 } label: {
                     Image(systemName: "ellipsis.circle")
                 }
+                // SwiftUI's macOS `Menu` doesn't reliably re-evaluate a
+                // `Toggle`'s checkmark against updated @Observable state on
+                // its own — without a fresh `.id()` per state combination,
+                // toggling Subscribed/Viewer Insights/Full Width kept
+                // showing the pre-toggle checkmark until the whole view was
+                // torn down and rebuilt (e.g. navigating away and back).
+                .id(menuIdentity)
             }
         }
         .task { await viewModel.loadFullContent() }
         .task {
             await viewModel.loadPinAndSubscriptionState()
         }
+        .task {
+            await viewModel.loadInsightsEnabledState()
+        }
         .task {
             while !Task.isCancelled {
                 await viewModel.loadViewers()
@@ -197,14 +230,34 @@ struct DocumentReaderView: View {
         .sheet(isPresented: $isShowingSearchSheet) {
             DocumentSearchSheet(apiClient: apiClient, document: document)
         }
-        .sheet(isPresented: $isShowingShareSheet) {
+        .sheet(isPresented: $isShowingNewDocumentSheet) {
-            DocumentShareSheet(apiClient: apiClient, documentId: viewModel.documentId)
+            NewDocumentSheet(apiClient: apiClient, initialParentDocument: document) { child in
+                onDocumentCreated()
+                onOpenChild(child)
             }
         }
+    }
+
+    /// Every toggle-backed piece of state shown as a checkmark inside
+    /// `menuContent` — see the `.id()` comment on the `Menu` above.
+    private var menuIdentity: String {
+        [
+            starStore.isStarred(documentId: viewModel.documentId),
+            viewModel.isSubscribed,
+            viewModel.isPinned,
+            viewModel.isInsightsEnabled ?? false,
+            viewModel.isFullWidth,
+            viewModel.isEditing,
+            isEffectivelyOnline
+        ].map(String.init).joined(separator: "-")
+    }
 
     @ViewBuilder
     private var viewerAvatars: some View {
-        if !viewModel.viewers.isEmpty {
+        // Tied to the Viewer Insights toggle — that's the feature this data
+        // belongs to, so turning it off should hide the avatars immediately
+        // rather than leaving them showing until the view reloads.
+        if viewModel.isInsightsEnabled == true, !viewModel.viewers.isEmpty {
             HStack(spacing: -6) {
                 ForEach(viewModel.viewers.prefix(5)) { viewer in
                     AvatarBadge(
@@ -249,48 +302,57 @@ struct DocumentReaderView: View {
         Button(starStore.isStarred(documentId: viewModel.documentId) ? "Unstar" : "Star") {
             Task { await star() }
         }
-        Button(viewModel.isSubscribed ? "Unsubscribe" : "Subscribe") {
+        Toggle("Subscribed", isOn: Binding(
-            Task { await toggleSubscription() }
+            get: { viewModel.isSubscribed },
-        }
+            set: { _ in Task { await toggleSubscription() } }
+        ))
 
         Divider()
 
         Button(viewModel.isEditing ? "Done Editing" : "Edit") {
             Task { await viewModel.toggleEditing() }
         }
-        // Sharing/membership management is its own subsystem, not a one-off
+        // Membership management now lives in DocumentShareSheet's "People
-        // action — deferred rather than half-built here.
+        // with access" section, alongside the share link — same sheet,
-        Button("Permissions…") {}
+        // same isShowingShareSheet state.
-            .disabled(true)
+        Button("Permissions…") {
+            isShowingShareSheet = true
+        }
+        .disabled(!isEffectivelyOnline)
 
         Divider()
 
         Button("Templatize") {
             Task { await templatize() }
         }
+        .disabled(!isEffectivelyOnline)
         Button("Duplicate") {
             Task { await duplicate() }
         }
+        .disabled(!isEffectivelyOnline)
         Button("Unpublish") {
             isShowingUnpublishConfirmation = true
         }
+        .disabled(!isEffectivelyOnline)
         Button("Archive…") {
             isShowingArchiveConfirmation = true
         }
+        .disabled(!isEffectivelyOnline)
 
         Divider()
 
         Button("Move") {
             isShowingMoveSheet = true
         }
+        .disabled(!isEffectivelyOnline)
         // Multipart file upload is its own subsystem — deferred rather than
         // half-built here.
         Button("Import Document…") {}
             .disabled(true)
         Button("New Document") {
-            Task { await createChildDocument() }
+            isShowingNewDocumentSheet = true
         }
-        Button(viewModel.isPinned ? "Unpin" : "Pin") {
+        Button(viewModel.isPinned ? "Unpin from Home" : "Pin to Home") {
             Task { await togglePin() }
         }
 
@@ -299,9 +361,13 @@ struct DocumentReaderView: View {
         Button("History") {
             isShowingHistorySheet = true
         }
+        .disabled(!isEffectivelyOnline)
         Button("Insights") {
             isShowingInsightsSheet = true
         }
+        .disabled(!isEffectivelyOnline)
+        // Present/Search in Document both read `documents.info`, which is
+        // read-through cached — they work offline on whatever's cached.
         Button("Present") {
             isShowingPresentSheet = true
         }
@@ -311,6 +377,7 @@ struct DocumentReaderView: View {
         Button("Download") {
             Task { await download() }
         }
+        .disabled(!isEffectivelyOnline)
         Button("Copy") {
             Task { await copyMarkdown() }
         }
@@ -323,21 +390,28 @@ struct DocumentReaderView: View {
 
         Divider()
 
-        Button("Enable Viewer Insights") {
+        Toggle("Viewer Insights", isOn: Binding(
-            Task { await enableInsights() }
+            get: { viewModel.isInsightsEnabled ?? false },
-        }
+            set: { _ in Task { await toggleInsights() } }
-        Button("Enable Embeds") {
+        ))
-            Task { await enableEmbeds() }
+        .disabled(!isEffectivelyOnline)
-        }
+        // Confirmed against a live server: there's no per-document embeds
-        Button(viewModel.isFullWidth ? "Default Width" : "Full Width") {
+        // field. Only a workspace-level setting exists, and that's not
-            Task { await toggleFullWidth() }
+        // reachable via the API either (no `team.update` endpoint in the
-        }
+        // vendored spec) — disabled rather than kept as a broken action.
+        Button("Enable Embeds") {}
+            .disabled(true)
+        Toggle("Full Width", isOn: Binding(
+            get: { viewModel.isFullWidth },
+            set: { _ in Task { await toggleFullWidth() } }
+        ))
 
         Divider()
 
         Button("Delete…", role: .destructive) {
             isShowingDeleteConfirmation = true
         }
+        .disabled(!isEffectivelyOnline)
     }
 
     private func star() async {
@@ -372,19 +446,11 @@ struct DocumentReaderView: View {
         }
     }
 
-    private func enableInsights() async {
+    private func toggleInsights() async {
         do {
-            try await viewModel.enableViewerInsights()
+            try await viewModel.toggleViewerInsights()
         } catch {
-            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't enable viewer insights.")
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't update viewer insights.")
-        }
-    }
-
-    private func enableEmbeds() async {
-        do {
-            try await viewModel.enableEmbeds()
-        } catch {
-            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't enable embeds.")
         }
     }
 
@@ -431,21 +497,6 @@ struct DocumentReaderView: View {
         }
     }
 
-    private func createChildDocument() async {
-        guard let collectionId = viewModel.collectionId else {
-            actionErrorMessage = "This document isn't in a collection."
-            return
-        }
-        do {
-            let child = try await apiClient.createDocument(
-                CreateDocumentRequest(title: "Untitled", text: "", collectionId: collectionId, parentDocumentId: viewModel.documentId)
-            )
-            onOpenChild(child)
-        } catch {
-            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't create a new document.")
-        }
-    }
-
     private func download() async {
         do {
             let markdown = try await apiClient.exportDocument(id: viewModel.documentId)

Outpost/Features/Collections/DocumentReaderViewModel.swift

@@ -28,7 +28,12 @@ final class DocumentReaderViewModel {
     private var pinId: String?
     private(set) var isSubscribed = false
     private var subscriptionId: String?
-    private(set) var share: OutlineShare?
+
+    /// `nil` until checked. Inferred from whether `documents.insights`
+    /// succeeds or fails — `insightsEnabled` isn't readable back off
+    /// `Document` in the vendored spec, so there's no direct field to read.
+    /// This is a heuristic, not confirmed server behavior.
+    private(set) var isInsightsEnabled: Bool?
 
     let documentId: String
     private let apiClient: OutlineAPIClient
@@ -75,7 +80,9 @@ final class DocumentReaderViewModel {
     }
 
     func loadPinAndSubscriptionState() async {
-        if let pins = try? await apiClient.listPins(ListPinsRequest(collectionId: collectionId)),
+        // `collectionId: nil` = Home pins. This menu's Pin action is "Pin to
+        // Home", not "Pin to Collection" — those are distinct on the server.
+        if let pins = try? await apiClient.listPins(ListPinsRequest(collectionId: nil)),
            let match = pins.first(where: { $0.documentId == documentId }) {
             isPinned = true
             pinId = match.id
@@ -94,8 +101,13 @@ final class DocumentReaderViewModel {
         }
     }
 
-    func loadShare() async {
+    func loadInsightsEnabledState() async {
-        share = try? await apiClient.shareInfo(documentId: documentId)
+        do {
+            _ = try await apiClient.documentInsights(DocumentInsightsRequest(id: documentId))
+            isInsightsEnabled = true
+        } catch {
+            isInsightsEnabled = false
+        }
     }
 
     func togglePin() async throws {
@@ -110,7 +122,7 @@ final class DocumentReaderViewModel {
                 throw error
             }
         } else {
-            let pin = try await apiClient.createPin(CreatePinRequest(documentId: documentId, collectionId: collectionId))
+            let pin = try await apiClient.createPin(CreatePinRequest(documentId: documentId, collectionId: nil))
             pinId = pin.id
             isPinned = true
         }
@@ -134,10 +146,6 @@ final class DocumentReaderViewModel {
         }
     }
 
-    func createOrLoadShare() async throws {
-        share = try await apiClient.createShare(CreateShareRequest(documentId: documentId))
-    }
-
     /// Turning editing off saves; turning it on is just a mode switch.
     func toggleEditing() async {
         guard isEditing else {
@@ -168,14 +176,14 @@ final class DocumentReaderViewModel {
         }
     }
 
-    /// Fire-and-forget: `insightsEnabled` isn't readable back off `Document`
+    func toggleViewerInsights() async throws {
-    /// in the vendored spec, so there's no state to reflect as a checkmark.
+        let newValue = !(isInsightsEnabled ?? false)
-    func enableViewerInsights() async throws {
+        isInsightsEnabled = newValue
-        _ = try await apiClient.updateDocument(UpdateDocumentRequest(id: documentId, insightsEnabled: true))
+        do {
+            _ = try await apiClient.updateDocument(UpdateDocumentRequest(id: documentId, insightsEnabled: newValue))
+        } catch {
+            isInsightsEnabled = !newValue
+            throw error
         }
-
-    /// Fire-and-forget, speculative field — see `UpdateDocumentRequest.documentEmbeds`.
-    func enableEmbeds() async throws {
-        _ = try await apiClient.updateDocument(UpdateDocumentRequest(id: documentId, documentEmbeds: true))
     }
 }

Outpost/Features/Collections/DocumentShareSheet.swift

@@ -3,68 +3,306 @@ import AppKit
 import SwiftUI
 import OutlineKit
 
+/// Content of the Share popover anchored to the reader toolbar's Share
+/// button (see `DocumentReaderView`'s `.popover(isPresented:)`). Was a
+/// modal `.sheet` originally — moved to a popover so it reads as "options
+/// for this button" instead of interrupting the whole window.
 @MainActor
 struct DocumentShareSheet: View {
-    @Environment(\.dismiss) private var dismiss
-
     let apiClient: OutlineAPIClient
     let documentId: String
 
     @State private var share: OutlineShare?
-    @State private var isLoading = false
+    @State private var titleOverride = ""
-    @State private var isUpdating = false
+    @State private var isLoadingShare = false
-    @State private var errorMessage: String?
+    @State private var isUpdatingShare = false
+    @State private var isRevoking = false
+    @State private var isShowingRevokeConfirmation = false
+    @State private var isShowingTitleField = false
+    @State private var shareErrorMessage: String?
     @State private var didCopy = false
 
+    @State private var members: [OutlineDocumentMember] = []
+    @State private var isLoadingMembers = false
+    @State private var isShowingAddPerson = false
+    @State private var userSearchQuery = ""
+    @State private var userSearchResults: [OutlineUser] = []
+    @State private var isSearchingUsers = false
+    @State private var selectedPermission = "read"
+    @State private var isAddingUser = false
+    @State private var actionErrorMessage: String?
+
     var body: some View {
-        VStack(alignment: .leading, spacing: 16) {
+        VStack(alignment: .leading, spacing: 0) {
-            HStack {
             Text("Share")
                 .font(.headline)
-                Spacer()
+                .padding(.horizontal, 16)
-                Button("Done") { dismiss() }
+                .padding(.top, 14)
+                .padding(.bottom, 10)
+
+            Divider()
+
+            ScrollView {
+                VStack(alignment: .leading, spacing: 18) {
+                    shareLinkSection
+                    peopleSection
+                }
+                .padding(16)
+            }
+            .frame(minHeight: 150, maxHeight: 900)
+        }
+        .frame(width: 280)
+        .task { await loadShare() }
+        .task { await loadMembers() }
+        .task(id: userSearchQuery) {
+            try? await Task.sleep(for: .milliseconds(250))
+            guard !Task.isCancelled else { return }
+            await searchUsers(userSearchQuery)
+        }
+        .confirmationDialog(
+            "Revoke this share link?",
+            isPresented: $isShowingRevokeConfirmation,
+            titleVisibility: .visible
+        ) {
+            Button("Revoke", role: .destructive) {
+                Task { await revoke() }
+            }
+            Button("Cancel", role: .cancel) {}
+        } message: {
+            Text("Anyone using this link will no longer be able to access the document.")
+        }
+        .alert("Couldn't Complete Action", isPresented: .constant(actionErrorMessage != nil)) {
+            Button("OK") { actionErrorMessage = nil }
+        } message: {
+            Text(actionErrorMessage ?? "")
+        }
     }
 
-            if isLoading {
+    // MARK: - Link section
-                ProgressView().frame(maxWidth: .infinity)
+
-            } else if let errorMessage {
+    @ViewBuilder
-                Text(errorMessage)
+    private var shareLinkSection: some View {
+        VStack(alignment: .leading, spacing: 8) {
+            sectionHeader(icon: "link", title: "Public Link")
+
+            if isLoadingShare {
+                ProgressView()
+                    .controlSize(.small)
+                    .frame(maxWidth: .infinity, alignment: .center)
+            } else if let shareErrorMessage {
+                Text(shareErrorMessage)
                     .font(.callout)
                     .foregroundStyle(.red)
             } else if let share {
-                HStack {
+                VStack(alignment: .leading, spacing: 6) {
-                    Text(share.url)
+                    if let url = share.url {
+                        HStack(spacing: 8) {
+                            Image(systemName: "globe")
+                                .foregroundStyle(.secondary)
+                                .font(.callout)
+                            Text(url)
                                 .font(.callout)
                                 .lineLimit(1)
                                 .truncationMode(.middle)
-                    Spacer()
+                            Spacer(minLength: 0)
                             Button {
-                        copyLink(share.url)
+                                copyLink(url)
                             } label: {
                                 Image(systemName: didCopy ? "checkmark" : "doc.on.doc")
+                                    .font(.callout)
+                            }
+                            .buttonStyle(.plain)
+                            .foregroundStyle(didCopy ? .green : .secondary)
+                            .help("Copy link")
+                        }
+                    }
+
+                    if isShowingTitleField {
+                        TextField("Public page title", text: $titleOverride)
+                            .textFieldStyle(.roundedBorder)
+                            .font(.callout)
+                            .disabled(isUpdatingShare)
+                            .onSubmit {
+                                Task { await setTitle(titleOverride) }
+                            }
+                    }
+                }
+                .padding(10)
+                .background(.fill.tertiary, in: RoundedRectangle(cornerRadius: 8))
+
+                HStack(spacing: 12) {
+                    Button(isShowingTitleField ? "Hide title field" : "Set public title") {
+                        isShowingTitleField.toggle()
+                    }
+                    .buttonStyle(.plain)
+                    .font(.caption)
+                    .foregroundStyle(.secondary)
+
+                    Spacer()
+
+                    Button("Revoke", role: .destructive) {
+                        isShowingRevokeConfirmation = true
+                    }
+                    .buttonStyle(.plain)
+                    .font(.caption)
+                    .foregroundStyle(.red)
+                    .disabled(isRevoking)
+                }
+            } else {
+                Button {
+                    Task { await create() }
+                } label: {
+                    Label("Create Share Link", systemImage: "link.badge.plus")
+                        .frame(maxWidth: .infinity)
+                }
+                .buttonStyle(.bordered)
+                .controlSize(.regular)
+            }
+        }
+    }
+
+    // MARK: - People section
+
+    @ViewBuilder
+    private var peopleSection: some View {
+        VStack(alignment: .leading, spacing: 8) {
+            HStack {
+                sectionHeader(icon: "person.2", title: "People with Access")
+                Spacer()
+                Button {
+                    isShowingAddPerson.toggle()
+                } label: {
+                    Image(systemName: isShowingAddPerson ? "xmark.circle.fill" : "person.badge.plus")
+                        .font(.callout)
+                }
+                .buttonStyle(.plain)
+                .foregroundStyle(.secondary)
+                .help("Add a person")
+            }
+
+            if isShowingAddPerson {
+                addPersonSection
+            }
+
+            if isLoadingMembers {
+                ProgressView()
+                    .controlSize(.small)
+                    .frame(maxWidth: .infinity, alignment: .center)
+            } else if members.isEmpty {
+                Text("No one else has explicit access yet.")
+                    .font(.callout)
+                    .foregroundStyle(.secondary)
+            } else {
+                VStack(spacing: 2) {
+                    ForEach(members) { member in
+                        memberRow(member)
+                    }
+                }
+            }
+        }
+    }
+
+    private func sectionHeader(icon: String, title: String) -> some View {
+        HStack(spacing: 6) {
+            Image(systemName: icon)
+                .font(.caption)
+                .foregroundStyle(.secondary)
+            Text(title)
+                .font(.caption.weight(.semibold))
+                .foregroundStyle(.secondary)
+                .textCase(.uppercase)
+        }
+    }
+
+    private var addPersonSection: some View {
+        VStack(alignment: .leading, spacing: 8) {
+            TextField("Search people by name or email", text: $userSearchQuery)
+                .textFieldStyle(.roundedBorder)
+
+            Picker("Permission", selection: $selectedPermission) {
+                Text("Can view").tag("read")
+                Text("Can edit").tag("read_write")
+            }
+            .pickerStyle(.segmented)
+            .labelsHidden()
+
+            if isSearchingUsers {
+                ProgressView()
+                    .controlSize(.small)
+                    .frame(maxWidth: .infinity, alignment: .center)
+            } else if !userSearchQuery.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty {
+                if userSearchResults.isEmpty {
+                    Text("No matches.")
+                        .font(.callout)
+                        .foregroundStyle(.secondary)
+                } else {
+                    VStack(spacing: 2) {
+                        ForEach(userSearchResults) { user in
+                            Button {
+                                Task { await addUser(user) }
+                            } label: {
+                                HStack(spacing: 8) {
+                                    avatar(for: user.name)
+                                    Text(user.name)
+                                        .font(.callout)
+                                    Spacer(minLength: 0)
+                                    Image(systemName: "plus.circle")
+                                        .foregroundStyle(.secondary)
+                                }
+                                .contentShape(Rectangle())
+                                .padding(.vertical, 4)
+                            }
+                            .buttonStyle(.plain)
+                            .disabled(isAddingUser)
+                        }
+                    }
+                }
+            }
+        }
+        .padding(10)
+        .background(.fill.tertiary, in: RoundedRectangle(cornerRadius: 8))
+    }
+
+    private func memberRow(_ member: OutlineDocumentMember) -> some View {
+        HStack(spacing: 8) {
+            avatar(for: member.name)
+            Text(member.name)
+                .font(.callout)
+            Spacer(minLength: 0)
+            if let permission = member.permission {
+                Text(permission == "read_write" ? "Can edit" : "Can view")
+                    .font(.caption)
+                    .foregroundStyle(.secondary)
+                    .padding(.horizontal, 6)
+                    .padding(.vertical, 2)
+                    .background(.fill.tertiary, in: Capsule())
+            }
+            Button {
+                Task { await removeUser(member) }
+            } label: {
+                Image(systemName: "xmark.circle.fill")
+                    .foregroundStyle(.secondary)
             }
             .buttonStyle(.plain)
         }
-                .padding(8)
+        .padding(.vertical, 4)
-                .background(.fill.tertiary, in: RoundedRectangle(cornerRadius: 6))
+    }
 
-                Toggle(
+    private func avatar(for name: String) -> some View {
-                    "Published — accessible without sign-in",
+        Circle()
-                    isOn: Binding(
+            .fill(.fill.secondary)
-                        get: { share.published },
+            .frame(width: 22, height: 22)
-                        set: { newValue in Task { await setPublished(newValue) } }
+            .overlay {
-                    )
+                Text(initials(for: name))
-                )
+                    .font(.system(size: 10, weight: .semibold))
-                .disabled(isUpdating)
+                    .foregroundStyle(.secondary)
-            } else {
-                Button("Create Share Link") {
-                    Task { await create() }
             }
     }
-        }
+
-        .padding(20)
+    private func initials(for name: String) -> String {
-        .frame(width: 380)
+        let parts = name.split(separator: " ").prefix(2)
-        .task { await load() }
+        let letters = parts.compactMap { $0.first }
+        return letters.isEmpty ? "?" : String(letters).uppercased()
     }
 
     private func copyLink(_ url: String) {
@@ -78,34 +316,96 @@ struct DocumentShareSheet: View {
         }
     }
 
-    private func load() async {
+    private func loadShare() async {
-        isLoading = true
+        isLoadingShare = true
-        defer { isLoading = false }
+        defer { isLoadingShare = false }
         do {
             share = try await apiClient.shareInfo(documentId: documentId)
+            titleOverride = share?.title ?? ""
         } catch {
-            errorMessage = outlineErrorMessage(error, fallback: "Couldn't load sharing info.")
+            shareErrorMessage = outlineErrorMessage(error, fallback: "Couldn't load sharing info.")
         }
     }
 
     private func create() async {
-        isLoading = true
+        isLoadingShare = true
-        defer { isLoading = false }
+        defer { isLoadingShare = false }
         do {
             share = try await apiClient.createShare(CreateShareRequest(documentId: documentId))
+            titleOverride = share?.title ?? ""
         } catch {
-            errorMessage = outlineErrorMessage(error, fallback: "Couldn't create a share link.")
+            shareErrorMessage = outlineErrorMessage(error, fallback: "Couldn't create a share link.")
         }
     }
 
-    private func setPublished(_ published: Bool) async {
+    private func setTitle(_ title: String) async {
         guard let share else { return }
-        isUpdating = true
+        let trimmed = title.trimmingCharacters(in: .whitespacesAndNewlines)
-        defer { isUpdating = false }
+        guard trimmed != (share.title ?? "") else { return }
+        isUpdatingShare = true
+        defer { isUpdatingShare = false }
         do {
-            self.share = try await apiClient.updateShare(UpdateShareRequest(id: share.id, published: published))
+            self.share = try await apiClient.updateShare(
+                UpdateShareRequest(id: share.id, published: share.published, title: trimmed)
+            )
         } catch {
-            errorMessage = outlineErrorMessage(error, fallback: "Couldn't update this share link.")
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't update this share link.")
+        }
+    }
+
+    private func revoke() async {
+        guard let share else { return }
+        isRevoking = true
+        defer { isRevoking = false }
+        do {
+            try await apiClient.revokeShare(id: share.id)
+            self.share = nil
+            titleOverride = ""
+            isShowingTitleField = false
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't revoke this share link.")
+        }
+    }
+
+    private func loadMembers() async {
+        isLoadingMembers = true
+        defer { isLoadingMembers = false }
+        members = (try? await apiClient.documentUsers(ListDocumentUsersRequest(id: documentId))) ?? []
+    }
+
+    private func searchUsers(_ query: String) async {
+        let trimmed = query.trimmingCharacters(in: .whitespacesAndNewlines)
+        guard !trimmed.isEmpty else {
+            userSearchResults = []
+            return
+        }
+        isSearchingUsers = true
+        defer { isSearchingUsers = false }
+        userSearchResults = (try? await apiClient.listUsers(ListUsersRequest(query: trimmed))) ?? []
+    }
+
+    private func addUser(_ user: OutlineUser) async {
+        isAddingUser = true
+        defer { isAddingUser = false }
+        do {
+            _ = try await apiClient.addDocumentUser(
+                AddDocumentUserRequest(id: documentId, userId: user.id, permission: selectedPermission)
+            )
+            userSearchQuery = ""
+            userSearchResults = []
+            isShowingAddPerson = false
+            await loadMembers()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't add this person.")
+        }
+    }
+
+    private func removeUser(_ member: OutlineDocumentMember) async {
+        do {
+            try await apiClient.removeDocumentUser(RemoveDocumentUserRequest(id: documentId, userId: member.id))
+            await loadMembers()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't remove this person.")
         }
     }
 }

Outpost/Features/Collections/NewDocumentSheet.swift

@@ -0,0 +1,169 @@
+#if os(macOS)
+import SwiftUI
+import OutlineKit
+
+/// The one shared "create a document" dialog — every "New Document" entry
+/// point (sidebar collection, sidebar document, reader toolbar/menu, Home)
+/// opens this instead of silently creating an "Untitled" document. Mirrors
+/// `MoveDocumentSheet`'s collection+parent picker pattern.
+@MainActor
+struct NewDocumentSheet: View {
+    @Environment(\.dismiss) private var dismiss
+
+    let apiClient: OutlineAPIClient
+    /// Pre-selected collection — e.g. opened from a specific collection's
+    /// "New Document". `nil` when opened from Home, where nothing is
+    /// pre-selected and the user must choose.
+    let initialCollectionID: String?
+    /// Pre-selected parent — e.g. opened from a document's "New Document",
+    /// which creates a child of that document.
+    let initialParentDocument: OutlineDocument?
+    let onCreated: (OutlineDocument) -> Void
+
+    @State private var title = ""
+    @State private var collections: [OutlineCollection] = []
+    @State private var selectedCollectionID: String?
+    @State private var rootDocuments: [OutlineDocument] = []
+    @State private var selectedParentID: String?
+    @State private var isLoadingCollections = false
+    @State private var isLoadingDestinationDocuments = false
+    @State private var isCreating = false
+    @State private var errorMessage: String?
+    @FocusState private var isTitleFocused: Bool
+
+    init(
+        apiClient: OutlineAPIClient,
+        initialCollectionID: String? = nil,
+        initialParentDocument: OutlineDocument? = nil,
+        onCreated: @escaping (OutlineDocument) -> Void
+    ) {
+        self.apiClient = apiClient
+        self.initialCollectionID = initialCollectionID
+        self.initialParentDocument = initialParentDocument
+        self.onCreated = onCreated
+    }
+
+    /// `rootDocuments` is only root-level (mirroring `MoveDocumentSheet`'s
+    /// intentionally shallow picker) — if the initial parent is nested
+    /// deeper than that, it wouldn't otherwise appear as a selectable option
+    /// even though it's already the selection.
+    private var parentOptions: [OutlineDocument] {
+        var options = rootDocuments
+        if let initialParentDocument,
+           initialParentDocument.collectionId == selectedCollectionID,
+           !options.contains(where: { $0.id == initialParentDocument.id }) {
+            options.insert(initialParentDocument, at: 0)
+        }
+        return options
+    }
+
+    var body: some View {
+        VStack(alignment: .leading, spacing: 16) {
+            Text("New Document")
+                .font(.headline)
+
+            TextField("Title", text: $title)
+                .textFieldStyle(.roundedBorder)
+                .focused($isTitleFocused)
+                .onSubmit { Task { await create() } }
+
+            if isLoadingCollections {
+                ProgressView().frame(maxWidth: .infinity)
+            } else {
+                Picker("Collection", selection: $selectedCollectionID) {
+                    Text("Choose a collection").tag(String?.none)
+                    ForEach(collections) { collection in
+                        Text(collection.name).tag(Optional(collection.id))
+                    }
+                }
+                .labelsHidden()
+
+                Picker("Location", selection: $selectedParentID) {
+                    Text("Collection root").tag(String?.none)
+                    ForEach(parentOptions) { candidate in
+                        Text(candidate.title.isEmpty ? "Untitled" : candidate.title).tag(Optional(candidate.id))
+                    }
+                }
+                .labelsHidden()
+                .disabled(selectedCollectionID == nil || isLoadingDestinationDocuments)
+            }
+
+            if let errorMessage {
+                Text(errorMessage)
+                    .font(.callout)
+                    .foregroundStyle(.red)
+            }
+
+            HStack {
+                Spacer()
+                Button("Cancel", role: .cancel) { dismiss() }
+                Button("Create") {
+                    Task { await create() }
+                }
+                .keyboardShortcut(.defaultAction)
+                .disabled(selectedCollectionID == nil || isCreating)
+            }
+        }
+        .padding(20)
+        .frame(width: 380)
+        .task {
+            await loadCollections()
+            selectedCollectionID = initialCollectionID ?? initialParentDocument?.collectionId ?? collections.first?.id
+            selectedParentID = initialParentDocument?.id
+            isTitleFocused = true
+        }
+        .task(id: selectedCollectionID) {
+            await loadRootDocuments()
+        }
+    }
+
+    private func loadCollections() async {
+        isLoadingCollections = true
+        defer { isLoadingCollections = false }
+        do {
+            collections = try await apiClient.listCollections(offset: 0, limit: 100)
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Couldn't load collections.")
+        }
+    }
+
+    private func loadRootDocuments() async {
+        guard let selectedCollectionID else {
+            rootDocuments = []
+            return
+        }
+        isLoadingDestinationDocuments = true
+        defer { isLoadingDestinationDocuments = false }
+        do {
+            rootDocuments = try await apiClient.listDocuments(
+                collectionId: selectedCollectionID,
+                parentDocumentId: nil,
+                offset: 0,
+                limit: 100
+            )
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Couldn't load destination documents.")
+        }
+    }
+
+    private func create() async {
+        guard let selectedCollectionID else { return }
+        isCreating = true
+        defer { isCreating = false }
+        do {
+            let document = try await apiClient.createDocument(
+                CreateDocumentRequest(
+                    title: title.isEmpty ? "Untitled" : title,
+                    text: "",
+                    collectionId: selectedCollectionID,
+                    parentDocumentId: selectedParentID
+                )
+            )
+            onCreated(document)
+            dismiss()
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Couldn't create this document.")
+        }
+    }
+}
+#endif

Outpost/Features/Collections/OfflineBanner.swift

@@ -0,0 +1,27 @@
+#if os(macOS)
+import SwiftUI
+
+/// Shown at the top of the sidebar whenever the app is offline — either for
+/// real (`NetworkMonitor` reports no connection) or because the user turned
+/// on the manual "Offline Mode" toggle. Cached collections/documents keep
+/// browsing working either way, but the user should know they might be
+/// looking at stale data.
+struct OfflineBanner: View {
+    /// Whether this is the user's own "Offline Mode" toggle rather than a
+    /// real dropped connection — same banner slot, different explanation.
+    var isManual: Bool = false
+
+    var body: some View {
+        HStack(spacing: 8) {
+            Image(systemName: "wifi.slash")
+                .foregroundStyle(.orange)
+            Text(isManual ? "Offline Mode — showing cached content" : "Offline — showing cached content")
+                .font(.callout)
+            Spacer(minLength: 0)
+        }
+        .padding(.horizontal, 12)
+        .padding(.vertical, 8)
+        .background(Color.orange.opacity(0.12))
+    }
+}
+#endif

Outpost/Features/Collections/OfflineConnectionPromptBanner.swift

@@ -0,0 +1,30 @@
+#if os(macOS)
+import SwiftUI
+
+/// Shown in the sidebar when the network is actually down and the user
+/// hasn't turned on Offline Mode themselves yet. Deliberately doesn't change
+/// any fetch behavior on its own — reads still try live and fall back to
+/// cache the normal way (see `CachingOutlineAPIClient`) until the user
+/// actually taps the button here, same as `RemoteChangesBanner` never
+/// auto-refreshes on their behalf either.
+struct OfflineConnectionPromptBanner: View {
+    let onEnableOfflineMode: () -> Void
+
+    var body: some View {
+        HStack(spacing: 8) {
+            Image(systemName: "wifi.slash")
+                .foregroundStyle(.orange)
+            Text("No connection")
+                .font(.callout)
+            Spacer(minLength: 8)
+            Button("Turn On Offline Mode", action: onEnableOfflineMode)
+                .buttonStyle(.borderedProminent)
+                .tint(.orange)
+                .controlSize(.small)
+        }
+        .padding(.horizontal, 12)
+        .padding(.vertical, 8)
+        .background(Color.orange.opacity(0.12))
+    }
+}
+#endif

Outpost/Features/Home/DocumentCardView.swift

@@ -0,0 +1,43 @@
+#if os(macOS)
+import SwiftUI
+import OutlineKit
+
+struct DocumentCardView: View {
+    @Environment(StarStore.self) private var starStore
+    let document: OutlineDocument
+
+    var body: some View {
+        VStack(alignment: .leading, spacing: 8) {
+            HStack {
+                if let emoji = document.emoji {
+                    Text(emoji)
+                        .font(.title2)
+                } else {
+                    Image(systemName: "doc.text")
+                        .font(.title3)
+                        .foregroundStyle(.secondary)
+                }
+                Spacer()
+                if starStore.isStarred(documentId: document.id) {
+                    Image(systemName: "star.fill")
+                        .font(.caption)
+                        .foregroundStyle(.yellow)
+                }
+            }
+
+            Text(document.title.isEmpty ? "Untitled" : document.title)
+                .font(.headline)
+                .lineLimit(2)
+                .multilineTextAlignment(.leading)
+                .frame(maxWidth: .infinity, alignment: .leading)
+
+            Text(document.updatedAt, format: .relative(presentation: .named))
+                .font(.caption)
+                .foregroundStyle(.secondary)
+        }
+        .padding(14)
+        .frame(maxWidth: .infinity, minHeight: 96, alignment: .topLeading)
+        .background(.fill.tertiary, in: RoundedRectangle(cornerRadius: 10))
+    }
+}
+#endif

Outpost/Features/Home/HomeTab.swift

@@ -0,0 +1,10 @@
+import Foundation
+
+enum HomeTab: String, CaseIterable, Identifiable {
+    case recentlyViewed = "Recently Viewed"
+    case popular = "Popular"
+    case recentlyUpdated = "Recently Updated"
+    case createdByMe = "Created by Me"
+
+    var id: String { rawValue }
+}

Outpost/Features/Home/HomeView.swift

@@ -0,0 +1,190 @@
+#if os(macOS)
+import SwiftUI
+import OutlineKit
+
+struct HomeView: View {
+    let apiClient: OutlineAPIClient
+    let onOpenDocument: (OutlineDocument) -> Void
+    /// Home has no sidebar row of its own to reload directly — this tells
+    /// the sidebar a document exists now so it can pick it up. See
+    /// `CollectionDocumentsOutline.externalRefreshToken`.
+    let onDocumentCreated: () -> Void
+
+    @State private var viewModel: HomeViewModel
+    @State private var selectedTab: HomeTab = .recentlyViewed
+    @State private var isShowingNewDocumentSheet = false
+
+    private let pinnedGridColumns = [GridItem(.adaptive(minimum: 260), spacing: 8)]
+    private let tabGridColumns = [GridItem(.adaptive(minimum: 220), spacing: 12)]
+
+    init(apiClient: OutlineAPIClient, onOpenDocument: @escaping (OutlineDocument) -> Void, onDocumentCreated: @escaping () -> Void) {
+        self.apiClient = apiClient
+        self.onOpenDocument = onOpenDocument
+        self.onDocumentCreated = onDocumentCreated
+        _viewModel = State(initialValue: HomeViewModel(apiClient: apiClient))
+    }
+
+    private var isShowingPinnedSection: Bool {
+        viewModel.isLoadingPinned || !viewModel.pinnedDocuments.isEmpty
+    }
+
+    var body: some View {
+        VStack(spacing: 0) {
+            if viewModel.hasRemoteChanges {
+                RemoteChangesBanner {
+                    Task {
+                        await viewModel.loadPinned()
+                        await viewModel.load(tab: selectedTab)
+                    }
+                }
+            }
+            // The pinned section claims roughly the top half when it has
+            // anything to show (scrolling within itself if there are enough
+            // pinned documents to overflow that), and collapses away entirely
+            // when there's nothing pinned so the tabs get the full height.
+            GeometryReader { proxy in
+                VStack(spacing: 0) {
+                    if isShowingPinnedSection {
+                        pinnedSection
+                            .frame(height: max(proxy.size.height / 2, 180))
+                        Divider()
+                    }
+                    tabSection
+                        .frame(maxWidth: .infinity, maxHeight: .infinity)
+                }
+            }
+        }
+        .toolbar {
+            ToolbarItem(placement: .primaryAction) {
+                Button {
+                    isShowingNewDocumentSheet = true
+                } label: {
+                    Image(systemName: "doc.badge.plus")
+                }
+                .help("New Document")
+            }
+        }
+        .sheet(isPresented: $isShowingNewDocumentSheet) {
+            NewDocumentSheet(apiClient: apiClient) { document in
+                onDocumentCreated()
+                onOpenDocument(document)
+            }
+        }
+        .task { await viewModel.loadPinned() }
+        .task(id: selectedTab) { await viewModel.load(tab: selectedTab) }
+        .task {
+            while !Task.isCancelled {
+                try? await Task.sleep(for: .seconds(45))
+                guard !Task.isCancelled else { break }
+                await viewModel.checkForRemoteChanges(tab: selectedTab)
+            }
+        }
+    }
+
+    private var pinnedSection: some View {
+        VStack(alignment: .leading, spacing: 12) {
+            Text("Pinned")
+                .font(.title3.weight(.semibold))
+                .padding(.horizontal, 24)
+                .padding(.top, 20)
+
+            if viewModel.isLoadingPinned {
+                ProgressView()
+                    .frame(maxWidth: .infinity, maxHeight: .infinity)
+            } else {
+                ScrollView {
+                    LazyVGrid(columns: pinnedGridColumns, spacing: 8) {
+                        ForEach(viewModel.pinnedDocuments) { document in
+                            Button {
+                                onOpenDocument(document)
+                            } label: {
+                                PinnedDocumentCard(document: document)
+                            }
+                            .buttonStyle(.plain)
+                        }
+                    }
+                    .padding(.horizontal, 24)
+                    .padding(.bottom, 16)
+                }
+            }
+        }
+    }
+
+    private var tabSection: some View {
+        VStack(alignment: .leading, spacing: 0) {
+            tabBar
+
+            Divider()
+
+            let documents = viewModel.documents(for: selectedTab)
+
+            Group {
+                if viewModel.isLoadingTab && documents.isEmpty {
+                    ProgressView()
+                        .frame(maxWidth: .infinity, maxHeight: .infinity)
+                } else if let errorMessage = viewModel.errorMessage, documents.isEmpty {
+                    ContentUnavailableView {
+                        Label("Couldn't Load Documents", systemImage: "exclamationmark.triangle")
+                    } description: {
+                        Text(errorMessage)
+                    } actions: {
+                        Button("Retry") {
+                            Task { await viewModel.load(tab: selectedTab) }
+                        }
+                    }
+                    .frame(maxWidth: .infinity, maxHeight: .infinity)
+                } else if documents.isEmpty {
+                    ContentUnavailableView(
+                        "No Documents",
+                        systemImage: "doc.text",
+                        description: Text("Nothing to show here yet.")
+                    )
+                    .frame(maxWidth: .infinity, maxHeight: .infinity)
+                } else {
+                    ScrollView {
+                        LazyVGrid(columns: tabGridColumns, spacing: 12) {
+                            ForEach(documents) { document in
+                                Button {
+                                    onOpenDocument(document)
+                                } label: {
+                                    DocumentCardView(document: document)
+                                }
+                                .buttonStyle(.plain)
+                            }
+                        }
+                        .padding(24)
+                    }
+                }
+            }
+            .frame(maxWidth: .infinity, maxHeight: .infinity)
+        }
+    }
+
+    // Mirrors `CollectionOverviewView.tabBar`'s exact style, rather than the
+    // native `.pickerStyle(.segmented)` this started with.
+    private var tabBar: some View {
+        HStack(spacing: 4) {
+            Spacer(minLength: 0)
+            ForEach(HomeTab.allCases) { tab in
+                Button {
+                    selectedTab = tab
+                } label: {
+                    Text(tab.rawValue)
+                        .font(.callout.weight(selectedTab == tab ? .semibold : .regular))
+                        .foregroundStyle(selectedTab == tab ? Color.primary : Color.secondary)
+                        .padding(.horizontal, 10)
+                        .padding(.vertical, 6)
+                        .background(
+                            selectedTab == tab ? Color.accentColor.opacity(0.15) : Color.clear,
+                            in: RoundedRectangle(cornerRadius: 6)
+                        )
+                }
+                .buttonStyle(.plain)
+            }
+            Spacer(minLength: 0)
+        }
+        .padding(.vertical, 10)
+        .frame(maxWidth: .infinity)
+    }
+}
+#endif

Outpost/Features/Home/HomeViewModel.swift

@@ -0,0 +1,143 @@
+import Foundation
+import Observation
+import OutlineKit
+
+@MainActor
+@Observable
+final class HomeViewModel {
+    private(set) var pinnedDocuments: [OutlineDocument] = []
+    private(set) var recentlyViewed: [OutlineDocument] = []
+    private(set) var popular: [OutlineDocument] = []
+    private(set) var recentlyUpdated: [OutlineDocument] = []
+    private(set) var createdByMe: [OutlineDocument] = []
+
+    var isLoadingPinned = false
+    var isLoadingTab = false
+    var errorMessage: String?
+    /// Drives a "Refresh" banner rather than silently swapping content out
+    /// from under whoever's looking at it — see `CollectionsViewModel`'s
+    /// identical pattern.
+    var hasRemoteChanges = false
+
+    private let apiClient: OutlineAPIClient
+    private var currentUserID: String?
+
+    init(apiClient: OutlineAPIClient) {
+        self.apiClient = apiClient
+    }
+
+    func documents(for tab: HomeTab) -> [OutlineDocument] {
+        switch tab {
+        case .recentlyViewed: recentlyViewed
+        case .popular: popular
+        case .recentlyUpdated: recentlyUpdated
+        case .createdByMe: createdByMe
+        }
+    }
+
+    func loadPinned() async {
+        isLoadingPinned = true
+        defer { isLoadingPinned = false }
+        pinnedDocuments = await fetchPinned()
+    }
+
+    func load(tab: HomeTab) async {
+        isLoadingTab = true
+        errorMessage = nil
+        defer { isLoadingTab = false }
+        do {
+            let documents = try await fetch(tab: tab)
+            set(documents, for: tab)
+            hasRemoteChanges = false
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Couldn't load documents.")
+        }
+    }
+
+    /// Fetches fresh pinned docs and the current tab's documents to compare
+    /// against what's displayed, without replacing either. Bails silently
+    /// on a fetch failure rather than treating it as "changed" — a
+    /// transient network hiccup (or, offline, `listPins` failing outright —
+    /// it isn't one of the cached endpoints) shouldn't pop the refresh
+    /// banner. This needs the *throwing* pinned-fetch specifically: the
+    /// plain `fetchPinned()` used elsewhere collapses any failure to `[]`,
+    /// which used to read here as "pins changed" against whatever was
+    /// already displayed and falsely popped the banner on every offline
+    /// poll.
+    func checkForRemoteChanges(tab: HomeTab) async {
+        async let freshPinnedTask = fetchPinnedThrowing()
+        guard let freshTab = try? await fetch(tab: tab) else { return }
+        guard let pinned = try? await freshPinnedTask else { return }
+        if Self.fingerprint(pinned) != Self.fingerprint(pinnedDocuments)
+            || Self.fingerprint(freshTab) != Self.fingerprint(documents(for: tab)) {
+            hasRemoteChanges = true
+        }
+    }
+
+    private func fetchPinned() async -> [OutlineDocument] {
+        (try? await fetchPinnedThrowing()) ?? []
+    }
+
+    /// `pins.list` only returns pin records, not the documents themselves —
+    /// fetches each pinned document individually. Pins are a small curated
+    /// set (unlike a full collection tree), so the N+1 here is acceptable
+    /// where it wouldn't be in the sidebar.
+    private func fetchPinnedThrowing() async throws -> [OutlineDocument] {
+        let pins = try await apiClient.listPins(ListPinsRequest(collectionId: nil))
+        var documents: [OutlineDocument] = []
+        for pin in pins {
+            if let document = try? await apiClient.documentInfo(id: pin.documentId) {
+                documents.append(document)
+            }
+        }
+        return documents
+    }
+
+    private func fetch(tab: HomeTab) async throws -> [OutlineDocument] {
+        switch tab {
+        case .recentlyViewed:
+            return try await apiClient.listViewedDocuments(offset: 0, limit: 25)
+        case .popular:
+            // `sort: "viewCount"` was a guess and the server rejected it
+            // outright ("sort: Invalid input") — sort is validated
+            // server-side against a fixed set, not free-form like the
+            // vendored spec's typing implies. Same conclusion as
+            // `CollectionTab.popular`: there's no real popularity
+            // ranking exposed via the REST API, so this falls back to
+            // the default list order rather than guessing again.
+            return try await apiClient.documentsList(DocumentsListRequest(limit: 25))
+        case .recentlyUpdated:
+            return try await apiClient.documentsList(
+                DocumentsListRequest(sort: "updatedAt", direction: "DESC", limit: 25)
+            )
+        case .createdByMe:
+            let userId = try await resolveCurrentUserID()
+            return try await apiClient.documentsList(
+                DocumentsListRequest(userId: userId, sort: "createdAt", direction: "DESC", limit: 25)
+            )
+        }
+    }
+
+    private func set(_ documents: [OutlineDocument], for tab: HomeTab) {
+        switch tab {
+        case .recentlyViewed: recentlyViewed = documents
+        case .popular: popular = documents
+        case .recentlyUpdated: recentlyUpdated = documents
+        case .createdByMe: createdByMe = documents
+        }
+    }
+
+    private func resolveCurrentUserID() async throws -> String {
+        if let currentUserID { return currentUserID }
+        let user = try await apiClient.currentUser()
+        currentUserID = user.id
+        return user.id
+    }
+
+    private static func fingerprint(_ documents: [OutlineDocument]) -> String {
+        documents
+            .map { "\($0.id):\($0.updatedAt.timeIntervalSince1970)" }
+            .sorted()
+            .joined(separator: "|")
+    }
+}

Outpost/Features/Home/PinnedDocumentCard.swift

@@ -0,0 +1,46 @@
+#if os(macOS)
+import SwiftUI
+import OutlineKit
+
+/// Deliberately distinct from `DocumentCardView` — the pinned section is for
+/// a quick scan of a small curated set, not browsing, so this is a dense
+/// single-line row rather than a tall card, with an explicit pin glyph so
+/// it doesn't read the same as the tab grids below it.
+struct PinnedDocumentCard: View {
+    @Environment(StarStore.self) private var starStore
+    let document: OutlineDocument
+
+    var body: some View {
+        HStack(spacing: 10) {
+            if let emoji = document.emoji {
+                Text(emoji)
+                    .font(.title3)
+            } else {
+                Image(systemName: "doc.text")
+                    .font(.body)
+                    .foregroundStyle(.secondary)
+            }
+
+            Text(document.title.isEmpty ? "Untitled" : document.title)
+                .font(.callout.weight(.medium))
+                .lineLimit(1)
+
+            Spacer(minLength: 0)
+
+            if starStore.isStarred(documentId: document.id) {
+                Image(systemName: "star.fill")
+                    .font(.caption2)
+                    .foregroundStyle(.yellow)
+            }
+
+            Image(systemName: "pin.fill")
+                .font(.caption2)
+                .foregroundStyle(.secondary)
+        }
+        .padding(.horizontal, 12)
+        .padding(.vertical, 9)
+        .frame(maxWidth: .infinity, alignment: .leading)
+        .background(.fill.tertiary, in: RoundedRectangle(cornerRadius: 8))
+    }
+}
+#endif

Outpost/OutpostApp.swift

@@ -14,10 +14,10 @@ import AppKit
 @main
 struct OutpostApp: App {
     @State private var session = SessionStore()
+    @State private var navigation = AppNavigation()
     @AppStorage("outpost.appearance") private var appearance: AppAppearance = .system
 
     #if os(macOS)
-    @Environment(\.openWindow) private var openWindow
     @State private var isShowingLogoutConfirmation = false
     #endif
 
@@ -25,6 +25,7 @@ struct OutpostApp: App {
         WindowGroup {
             RootView()
                 .environment(session)
+                .environment(navigation)
                 #if os(iOS)
                 .preferredColorScheme(appearance.colorScheme)
                 #endif
@@ -38,9 +39,20 @@ struct OutpostApp: App {
         .commands {
             CommandGroup(replacing: .appInfo) {
                 Button("About Outpost") {
-                    openWindow(id: "about")
+                    navigation.selectedSettingsSection = .about
+                    navigation.isShowingSettings = true
                 }
             }
+            // No `Settings {}` scene anymore — Settings renders inside the
+            // root window (see `AppNavigation`), not a separate popup, so
+            // ⌘, has to be wired up by hand instead of coming for free.
+            CommandGroup(replacing: .appSettings) {
+                Button("Settings…") {
+                    navigation.isShowingSettings = true
+                }
+                .keyboardShortcut(",")
+                .disabled(!session.isSignedIn)
+            }
             CommandGroup(after: .appSettings) {
                 Divider()
                 Button("Log Out…") {
@@ -52,22 +64,11 @@ struct OutpostApp: App {
         #endif
 
         #if os(macOS)
-        Window("About Outpost", id: "about") {
-            AboutView()
-                .disablesFullScreen()
-        }
-        .windowResizability(.contentSize)
-
         Window("Keyboard Shortcuts", id: "keyboard-shortcuts") {
             KeyboardShortcutsView()
                 .disablesFullScreen()
         }
         .windowResizability(.contentSize)
-
-        Settings {
-            PreferencesView()
-                .environment(session)
-        }
         #endif
     }
 

Outpost/Root/AppNavigation.swift

@@ -0,0 +1,137 @@
+import Observation
+
+/// Top-level groupings shown as section headers in `SettingsSidebarList`.
+/// `general` holds everything that's ours, not Outline's own settings
+/// categories — labeled "Outpost" so it reads as clearly distinct from the
+/// Outline-sourced groups below it.
+enum SettingsCategory: String, CaseIterable, Identifiable {
+    case general
+    case account
+    case workspace
+
+    var id: String { rawValue }
+
+    var title: String? {
+        switch self {
+        case .general: return "Outpost"
+        case .account: return "Account"
+        case .workspace: return "Workspace"
+        }
+    }
+}
+
+/// One entry in the Settings sidebar. Mirrors Outline's own settings
+/// categories (Account/Workspace) so this app's settings read as a native
+/// counterpart to the web app's, plus a `general` group for things that are
+/// ours and don't map onto Outline's structure (offline/sync, advanced,
+/// about, appearance). Outline's own version info moved to the sidebar
+/// footer (`SettingsSidebarList`) instead of a standalone
+/// Integrations & Installation section.
+///
+/// Most of the Account/Workspace cases are navigation-only for now —
+/// `SettingsView` renders a "Coming Soon" placeholder for anything not
+/// explicitly built yet. Content lands section by section.
+enum SettingsSection: String, CaseIterable, Identifiable, Hashable {
+    // General (ours)
+    case appearance, offlineSync, advanced, about
+
+    // Account
+    case profile, preferences, notifications, passkeys, apiAccess
+
+    // Workspace
+    case details, authentication, security, ai, members, groups, templates, emojis, applications, shared, links, webhooks, importData, exportData
+
+    var id: String { rawValue }
+
+    var category: SettingsCategory {
+        switch self {
+        case .appearance, .offlineSync, .advanced, .about:
+            return .general
+        case .profile, .preferences, .notifications, .passkeys, .apiAccess:
+            return .account
+        case .details, .authentication, .security, .ai, .members, .groups, .templates, .emojis, .applications, .shared, .links, .webhooks, .importData, .exportData:
+            return .workspace
+        }
+    }
+
+    var title: String {
+        switch self {
+        case .appearance: return "Appearance"
+        case .offlineSync: return "Offline & Sync"
+        case .advanced: return "Advanced"
+        case .about: return "About"
+        case .profile: return "Profile"
+        case .preferences: return "Preferences"
+        case .notifications: return "Notifications"
+        case .passkeys: return "Passkeys"
+        case .apiAccess: return "API & Access"
+        case .details: return "Details"
+        case .authentication: return "Authentication"
+        case .security: return "Security"
+        case .ai: return "AI"
+        case .members: return "Members"
+        case .groups: return "Groups"
+        case .templates: return "Templates"
+        case .emojis: return "Emojis"
+        case .applications: return "Applications"
+        case .shared: return "Shared"
+        case .links: return "Links"
+        case .webhooks: return "Webhooks"
+        case .importData: return "Import"
+        case .exportData: return "Export"
+        }
+    }
+
+    var icon: String {
+        switch self {
+        case .appearance: return "paintbrush"
+        case .offlineSync: return "arrow.triangle.2.circlepath"
+        case .advanced: return "wrench.and.screwdriver"
+        case .about: return "info.circle"
+        case .profile: return "person.crop.circle"
+        case .preferences: return "gearshape"
+        case .notifications: return "bell"
+        case .passkeys: return "key"
+        case .apiAccess: return "chevron.left.forwardslash.chevron.right"
+        case .details: return "building.2"
+        case .authentication: return "lock"
+        case .security: return "shield"
+        case .ai: return "sparkles"
+        case .members: return "person.2"
+        case .groups: return "person.3"
+        case .templates: return "doc.on.doc"
+        case .emojis: return "face.smiling"
+        case .applications: return "app.badge"
+        case .shared: return "square.and.arrow.up.on.square"
+        case .links: return "link"
+        case .webhooks: return "bolt.horizontal"
+        case .importData: return "square.and.arrow.down"
+        case .exportData: return "square.and.arrow.up"
+        }
+    }
+
+    /// Everything actually built so far — everything else in Account/
+    /// Workspace renders a "Coming Soon" placeholder until its content is
+    /// specified and built.
+    var isImplemented: Bool {
+        switch self {
+        case .appearance, .offlineSync, .advanced, .about, .profile, .preferences, .notifications, .passkeys, .apiAccess:
+            return true
+        default:
+            return false
+        }
+    }
+}
+
+/// Cross-cutting UI state that doesn't belong to any one screen. Lives at
+/// `OutpostApp` (so both `RootView`'s content and its `⌘,` command can reach
+/// it) and is read wherever something needs to open Settings (the profile
+/// menu) or render it — as a swap of the *existing* sidebar/detail panes in
+/// `ContentView_macOS`, not a separate popup window or an overlay that hides
+/// the sidebar.
+@Observable
+@MainActor
+final class AppNavigation {
+    var isShowingSettings = false
+    var selectedSettingsSection: SettingsSection? = .appearance
+}

Outpost/Root/RootView.swift

@@ -5,6 +5,19 @@ struct RootView: View {
     @Environment(SessionStore.self) private var session
     @State private var welcomeName: String?
     @State private var starStore = StarStore()
+    @AppStorage("outpost.fullLocalSyncEnabled") private var isFullLocalSyncEnabled = false
+    @AppStorage(CachingOutlineAPIClient.offlineModeDefaultsKey) private var isOfflineModeEnabled = false
+
+    /// Real connectivity is only half of "can talk to the server" — the
+    /// manual Offline Mode toggle is the other half. Syncing needs to
+    /// resume on either one clearing, not just a real reconnect: turning
+    /// the toggle off while the network had been up the whole time never
+    /// changes `networkMonitor.isOnline`, so keying the flush task off that
+    /// alone left pending operations stuck until the next real network
+    /// blip.
+    private var isEffectivelyOnline: Bool {
+        session.networkMonitor.isOnline && !isOfflineModeEnabled
+    }
 
     var body: some View {
         ZStack {
@@ -32,6 +45,48 @@ struct RootView: View {
                 starStore.reset()
             }
         }
+        // Replay whatever queued up while offline the moment either signal
+        // clears — a real reconnect, or the user turning Offline Mode back
+        // off — no need to wait for the user to open Settings and hit Retry.
+        // Also catches Full Local Sync back up immediately, rather than
+        // leaving it to wait out the rest of the periodic loop below.
+        //
+        // The flush itself gets a retry loop with a cooloff, not just one
+        // attempt: a single transient failure (one bad operation, a blip
+        // mid-flush) used to leave everything else stuck until the user
+        // manually hit Retry or connectivity changed again. Keeps retrying
+        // every 5 minutes for as long as *anything* is still pending and
+        // this signal stays on — stops on its own once the queue is empty,
+        // and `.task(id:)` cancels/restarts it automatically if
+        // isEffectivelyOnline flips again in the meantime.
+        .task(id: isEffectivelyOnline) {
+            guard isEffectivelyOnline, let cachingClient = session.cachingClient else { return }
+            if isFullLocalSyncEnabled {
+                _ = await cachingClient.performFullSync()
+            }
+            while !Task.isCancelled {
+                _ = await cachingClient.flushPendingOperations()
+                let remaining = await cachingClient.pendingOperations()
+                guard !remaining.isEmpty else { break }
+                try? await Task.sleep(for: .seconds(300))
+            }
+        }
+        // Fully automatic — this is the only place Full Local Sync actually
+        // runs from (Settings' "Sync Now" is just an on-demand nudge at the
+        // same call). Syncs immediately whenever this task (re)starts, which
+        // covers both "just switched on" and "was already on at launch" —
+        // `.task(id:)` restarts on either, an `@AppStorage`-backed toggle
+        // changing anywhere updates every view reading that key — then every
+        // 20 minutes after, for as long as it stays enabled.
+        .task(id: isFullLocalSyncEnabled) {
+            guard isFullLocalSyncEnabled else { return }
+            while !Task.isCancelled {
+                if isEffectivelyOnline, let cachingClient = session.cachingClient {
+                    _ = await cachingClient.performFullSync()
+                }
+                try? await Task.sleep(for: .seconds(1200))
+            }
+        }
     }
 
     private func startWelcomeTransition(_ result: AuthViewModel.AuthResult) {

Outpost/Root/SessionStore.swift

@@ -11,12 +11,26 @@ final class SessionStore {
     private let defaults: UserDefaults
 
     var isSignedIn: Bool
+    private(set) var userId: String?
     var userName: String?
     var userEmail: String?
     var userAvatarURL: URL?
+    var userLanguage: String?
+    var userPreferences: OutlineUserPreferences?
+    var userNotificationSettings: [String: Bool]?
     var teamName: String?
     var teamAvatarURL: URL?
     private(set) var apiClient: OutlineAPIClient?
+    /// Same object as `apiClient` when the offline cache is available — kept
+    /// as a separately-typed reference so Settings can reach cache/sync-queue
+    /// specific methods (`flushPendingOperations`, `performFullSync`, etc.)
+    /// without downcasting the protocol-typed `apiClient` everywhere.
+    private(set) var cachingClient: CachingOutlineAPIClient?
+    let networkMonitor = NetworkMonitor()
+    /// `nil` only if the on-disk SwiftData store failed to open (e.g. disk
+    /// full) — in that case `apiClient` falls back to talking to the server
+    /// directly with no offline cache, rather than failing sign-in outright.
+    private let cacheStore: OfflineCacheStore?
 
     var serverURL: URL? {
         defaults.string(forKey: Self.serverURLDefaultsKey).flatMap(URL.init(string:))
@@ -25,36 +39,66 @@ final class SessionStore {
     init(tokenStore: TokenStoring = KeychainTokenStore(), defaults: UserDefaults = .standard) {
         self.tokenStore = tokenStore
         self.defaults = defaults
-        self.isSignedIn = (try? tokenStore.token()) != nil
+        self.cacheStore = (try? OfflineCacheStore.makeContainer()).map(OfflineCacheStore.init(modelContainer:))
 
-        if isSignedIn, let serverURL {
+        let hasToken = (try? tokenStore.token()) != nil
-            apiClient = LiveOutlineAPIClient(
+        let storedServerURL = defaults.string(forKey: Self.serverURLDefaultsKey).flatMap(URL.init(string:))
-                configuration: OutlineConfiguration(baseURL: serverURL),
+
-                tokenStore: tokenStore
+        if hasToken, let storedServerURL {
-            )
+            isSignedIn = true
+            (apiClient, cachingClient) = Self.makeAPIClient(serverURL: storedServerURL, tokenStore: tokenStore, cache: cacheStore)
+        } else {
+            // Keychain and the sandboxed UserDefaults container don't
+            // always survive together — a Keychain item written by an
+            // older-signed build can outlive a reinstall that wipes the
+            // container (or vice versa), leaving a token with no server or
+            // a server with no token. Clear whichever half survived rather
+            // than showing a broken "signed in" UI with no working
+            // apiClient — a fresh sign-in rewrites both consistently.
+            if hasToken {
+                try? tokenStore.clear()
+            }
+            defaults.removeObject(forKey: Self.serverURLDefaultsKey)
+            isSignedIn = false
         }
     }
 
     func signIn(serverURL: URL, user: OutlineUser, team: OutlineTeam) {
         defaults.set(serverURL.absoluteString, forKey: Self.serverURLDefaultsKey)
-        apiClient = LiveOutlineAPIClient(
+        (apiClient, cachingClient) = Self.makeAPIClient(serverURL: serverURL, tokenStore: tokenStore, cache: cacheStore)
+        apply(user: user, team: team, serverURL: serverURL)
+        isSignedIn = true
+    }
+
+    private static func makeAPIClient(
+        serverURL: URL,
+        tokenStore: TokenStoring,
+        cache: OfflineCacheStore?
+    ) -> (OutlineAPIClient, CachingOutlineAPIClient?) {
+        let live = LiveOutlineAPIClient(
             configuration: OutlineConfiguration(baseURL: serverURL),
             tokenStore: tokenStore
         )
-        apply(user: user, team: team, serverURL: serverURL)
+        guard let cache else { return (live, nil) }
-        isSignedIn = true
+        let caching = CachingOutlineAPIClient(live: live, cache: cache)
+        return (caching, caching)
     }
 
     func signOut() {
         try? tokenStore.clear()
         defaults.removeObject(forKey: Self.serverURLDefaultsKey)
         isSignedIn = false
+        userId = nil
         userName = nil
         userEmail = nil
         userAvatarURL = nil
+        userLanguage = nil
+        userPreferences = nil
+        userNotificationSettings = nil
         teamName = nil
         teamAvatarURL = nil
         apiClient = nil
+        cachingClient = nil
     }
 
     /// Re-fetches user/workspace name/logo on relaunch, when the token survived but this
@@ -65,13 +109,30 @@ final class SessionStore {
         apply(user: auth.user, team: auth.team, serverURL: serverURL)
     }
 
+    /// Settings calls this after a successful name/avatar change so the
+    /// sidebar's account footer and everywhere else reading these reflect
+    /// it immediately, without waiting for the next `auth.info` refresh.
+    func applyUpdatedProfile(_ user: OutlineUser) {
+        guard let serverURL else { return }
+        userId = user.id
+        userName = user.name
+        userAvatarURL = user.avatarUrl.flatMap { URL(string: $0, relativeTo: serverURL)?.absoluteURL }
+        userLanguage = user.language
+        userPreferences = user.preferences
+        userNotificationSettings = user.notificationSettings
+    }
+
     private func apply(user: OutlineUser, team: OutlineTeam, serverURL: URL) {
+        userId = user.id
         userName = user.name
         userEmail = user.email
         // Outline can return either an absolute URL or a server-relative path
         // (e.g. `/api/files.get?key=...`) for avatarUrl — resolve against the
         // configured server so relative paths don't fail as "unsupported URL".
         userAvatarURL = user.avatarUrl.flatMap { URL(string: $0, relativeTo: serverURL)?.absoluteURL }
+        userLanguage = user.language
+        userPreferences = user.preferences
+        userNotificationSettings = user.notificationSettings
         teamName = team.name
         teamAvatarURL = team.avatarUrl.flatMap { URL(string: $0, relativeTo: serverURL)?.absoluteURL }
     }

Outpost/Support/AvatarBadge.swift

@@ -1,4 +1,5 @@
 import SwiftUI
+import OutlineKit
 
 #if os(macOS)
 import AppKit
@@ -41,11 +42,46 @@ struct AvatarBadge: View {
         .task(id: avatarURL) {
             loadedImage = nil
             guard let avatarURL else { return }
-            guard let (data, _) = try? await URLSession.shared.data(from: avatarURL) else { return }
+            loadedImage = await Self.loadImage(from: avatarURL)
-            loadedImage = PlatformImage(data: data)
         }
     }
 
+    /// The real fix, confirmed against a live network capture: every other
+    /// request this app makes attaches `Authorization: Bearer <token>` —
+    /// this one never did, sending a bare unauthenticated GET. Outline's
+    /// browser session authenticates `attachments.redirect` via cookies
+    /// instead, which a native app doesn't have; the API-token equivalent
+    /// is the same Bearer header every RPC call already uses. Almost
+    /// certainly means no avatar image (not just a freshly-uploaded one)
+    /// has ever actually loaded in this app — a 401 and a "no avatar set"
+    /// look identical here, both just fall back to the placeholder icon
+    /// with nothing on screen to flag it as an error.
+    ///
+    /// The retry loop is a secondary, independent hardening — cheap
+    /// insurance against a self-hosted reverse-proxied storage backend not
+    /// being instantly consistent right after an upload — kept alongside
+    /// the auth fix rather than instead of it.
+    private static func loadImage(from url: URL) async -> PlatformImage? {
+        var request = URLRequest(url: url)
+        request.cachePolicy = .reloadIgnoringLocalCacheData
+        if let token = try? KeychainTokenStore().token() {
+            request.setValue("Bearer \(token)", forHTTPHeaderField: "Authorization")
+        }
+
+        for attempt in 0..<3 {
+            if attempt > 0 {
+                try? await Task.sleep(for: .milliseconds(400))
+            }
+            if let (data, response) = try? await URLSession.shared.data(for: request),
+               let httpResponse = response as? HTTPURLResponse,
+               (200...299).contains(httpResponse.statusCode),
+               let image = PlatformImage(data: data) {
+                return image
+            }
+        }
+        return nil
+    }
+
     private func platformImage(_ image: PlatformImage) -> Image {
         #if os(macOS)
         Image(nsImage: image)

Outpost/Support/NSImage+JPEGData.swift

@@ -0,0 +1,14 @@
+#if os(macOS)
+import AppKit
+
+extension NSImage {
+    /// `NSImage` has no built-in JPEG encoder (unlike `UIImage`) — routes
+    /// through a bitmap representation to get one.
+    func jpegData(compressionQuality: CGFloat) -> Data? {
+        guard let tiffData = tiffRepresentation, let bitmap = NSBitmapImageRep(data: tiffData) else {
+            return nil
+        }
+        return bitmap.representation(using: .jpeg, properties: [.compressionFactor: compressionQuality])
+    }
+}
+#endif

Outpost/Support/NetworkMonitor.swift

@@ -0,0 +1,36 @@
+import Foundation
+import Network
+import Observation
+
+/// Backs the sidebar's offline badge — purely a UI signal. Unrelated to
+/// `CachingOutlineAPIClient`'s own fallback logic, which reacts to actual
+/// request failures rather than pre-checking reachability.
+@Observable
+@MainActor
+final class NetworkMonitor {
+    private(set) var isOnline = true
+
+    private let monitor = NWPathMonitor()
+    private let queue = DispatchQueue(label: "com.outpost.network-monitor")
+
+    init() {
+        // Weak on the outer closure (it's held by `monitor` for the object's
+        // whole lifetime, so a strong capture here would be a retain cycle),
+        // then unwrapped once into a plain strong local — the inner `Task`
+        // closure capturing that local `self` is what a nested closure needs
+        // to be consistent about capture semantics with its enclosing one.
+        monitor.pathUpdateHandler = { [weak self] path in
+            guard let self else { return }
+     
+            let online = path.status == .satisfied
+            Task { @MainActor in
+                self.isOnline = online
+            }
+        }
+        monitor.start(queue: queue)
+    }
+
+    deinit {
+        monitor.cancel()
+    }
+}

Outpost/Support/OutlineLocale.swift

@@ -0,0 +1,35 @@
+import Foundation
+
+/// Outline's interface-language options. Not exhaustive — Outline accepts
+/// community translations via its own translation portal, so the real list
+/// on any given server can be longer than this; this covers the common
+/// cases and falls back to showing whatever code the server already has
+/// set even if it isn't in this list.
+struct OutlineLocale: Identifiable, Hashable {
+    let code: String
+    let label: String
+
+    var id: String { code }
+
+    static let all: [OutlineLocale] = [
+        OutlineLocale(code: "en_US", label: "English (US)"),
+        OutlineLocale(code: "en_GB", label: "English (UK)"),
+        OutlineLocale(code: "de_DE", label: "Deutsch"),
+        OutlineLocale(code: "fr_FR", label: "Français"),
+        OutlineLocale(code: "es_ES", label: "Español"),
+        OutlineLocale(code: "pt_PT", label: "Português"),
+        OutlineLocale(code: "pt_BR", label: "Português (Brasil)"),
+        OutlineLocale(code: "it_IT", label: "Italiano"),
+        OutlineLocale(code: "nl_NL", label: "Nederlands"),
+        OutlineLocale(code: "pl_PL", label: "Polski"),
+        OutlineLocale(code: "ru_RU", label: "Русский"),
+        OutlineLocale(code: "ja_JP", label: "日本語"),
+        OutlineLocale(code: "ko_KR", label: "한국어"),
+        OutlineLocale(code: "zh_CN", label: "中文 (简体)"),
+        OutlineLocale(code: "zh_TW", label: "中文 (繁體)"),
+    ]
+
+    static func label(for code: String) -> String {
+        all.first(where: { $0.code == code })?.label ?? code
+    }
+}

Outpost/Support/OutpostVersion.swift

@@ -0,0 +1,31 @@
+import Foundation
+
+/// Single source of truth for how Outpost's own version is formatted —
+/// used by both the About page and the Settings sidebar footer, so they
+/// can't drift out of sync the way `AboutInfoView` was already written to
+/// avoid for its own two call sites.
+enum OutpostVersion {
+    /// Bumped alongside `MARKETING_VERSION` in the Xcode project — kept out
+    /// of the bundle version itself since `CFBundleShortVersionString` is
+    /// expected to stay a plain dotted-numeric string, not `0.0.1-ALPHA`.
+    static let releaseStage = "ALPHA"
+
+    static var shortVersion: String {
+        Bundle.main.object(forInfoDictionaryKey: "CFBundleShortVersionString") as? String ?? "0.0.1"
+    }
+
+    static var buildNumber: String {
+        Bundle.main.object(forInfoDictionaryKey: "CFBundleVersion") as? String ?? "1"
+    }
+
+    /// e.g. `"0.0.3-ALPHA"` — for compact display (sidebar footer).
+    static var displayString: String {
+        let stageSuffix = releaseStage.isEmpty ? "" : "-\(releaseStage)"
+        return "\(shortVersion)\(stageSuffix)"
+    }
+
+    /// e.g. `"Version 0.0.3-ALPHA (1)"` — for the About page.
+    static var fullVersionString: String {
+        "Version \(displayString) (\(buildNumber))"
+    }
+}

README.md

@@ -1,27 +1,29 @@
-# Outpost
+<p align="center">
+  <img src="Outpost/Assets.xcassets/AppLogo.imageset/outpost-ios-1024.png" width="120" alt="Outpost logo">
+</p>
+
+<h1 align="center">Outpost</h1>
+
+<p align="center">
+  <a href="https://testflight.apple.com/join/y1mYcYAM">
+    <img src="https://img.shields.io/badge/Download-TestFlight-0D96F6?style=for-the-badge&logo=apple&logoColor=white" alt="Download on TestFlight">
+  </a>
+</p>
 
 A native Apple ecosystem client for [Outline](https://github.com/outline/outline) — built for iOS, iPadOS, and macOS from a single SwiftUI codebase, aiming for full editing parity with Outline's web app, including realtime collaborative editing.
 
+> **Early alpha — macOS only for now.** Expect missing features and rough edges. iOS/iPadOS support is planned but not in the current build. See the [releases page](https://git.psmattas.com/psmattas/Outpost/releases) for changelogs, and [open an issue](https://git.psmattas.com/psmattas/Outpost/issues) if you hit anything.
+
 ## Why
 
 Outline's web app is great, but there's no native Apple client with full editing parity. This project connects to a self-hosted Outline instance over its REST API and realtime collaboration socket to provide a proper native experience across the Apple ecosystem.
 
-## Status
-
-Early development. See `CLAUDE.md` for the current architecture and phased build plan.
-
-- [ ] Phase 1 — Auth, browse, search, REST-only editing
-- [ ] Phase 2 — Realtime collaborative editing (Yjs/Hocuspocus)
-- [ ] Phase 3 — Offline cache, tables, embeds, comments, macOS polish
-
 ## Requirements
 
-- Xcode 16+
+- Xcode 27+ (currently developed against an Xcode 27 beta — this is a hard minimum, not a suggestion)
-- iOS 17+ / iPadOS 17+ / macOS 14+
+- macOS 27+. iOS/iPadOS support is planned but not in the current build (see the alpha note above) — same 27+ minimum will apply once it lands
 - A self-hosted (or hosted) Outline instance with API access
 
-> They will be updated. These are old requirements.
-
 ## Setup
 
 1. Clone the repo and open the `.xcodeproj` in Xcode.
@@ -42,6 +44,16 @@ Parts of this codebase are AI-assisted (built with the help of AI coding tools).
 
 This project is a client only — it does not include, vendor, or redistribute any of Outline's (BSL 1.1 licensed) server source. See [`LICENSE`](./LICENSE) for this repository's own license.
 
+## Privacy
+
+Outpost collects nothing about you — no analytics, no telemetry, no crash reporting of its own, no age or demographic data, nothing. The only thing stored locally is your Outline server URL and API token (in the device Keychain) and, optionally, a local offline cache of what you've viewed. Everything else goes straight from your device to whatever Outline server you configure — there's no backend in between, and the developer has no access to your data or your server.
+
+Full policy, terms of service, and data-processing statement are on the [wiki](https://git.psmattas.com/psmattas/Outpost/wiki):
+
+- [Privacy Policy](https://git.psmattas.com/psmattas/Outpost/wiki/Privacy-Policy.-)
+- [Terms of Service](https://git.psmattas.com/psmattas/Outpost/wiki/Terms-of-Service.-)
+- [Data Processing Statement](https://git.psmattas.com/psmattas/Outpost/wiki/Data-Processing-Statement.-)
+
 ## Not affiliated with Outline
 
 This is an independent, unofficial client. Not affiliated with or endorsed by General Outline, Inc.

SECURITY.md

@@ -0,0 +1,38 @@
+# Security Policy
+
+## Reporting a Vulnerability
+
+If you discover a security vulnerability in Outpost, please do **not**
+open a public issue.
+
+Report it privately to: **security@psmattas.com**
+
+Include:
+- A description of the vulnerability
+- Steps to reproduce
+- Potential impact
+- Any suggested fixes if available
+
+We will acknowledge receipt within 48 hours and aim to release a fix
+within 14 days depending on severity.
+
+## Supported Versions
+
+Outpost is in early alpha (`0.0.x`) — there's no stable release line
+yet. Only the most recent tagged release receives fixes; please make
+sure you're on the latest alpha before reporting.
+
+| Version | Supported |
+| :--- | :---: |
+| Latest tagged release | ✅ |
+| Older releases | ❌ |
+
+## Scope
+
+Outpost is a client application that talks to a self-hosted Outline
+instance you control — it doesn't run any server infrastructure of its
+own. Vulnerabilities in Outline itself belong to
+[outline/outline](https://github.com/outline/outline), not this repo.
+API tokens are stored in the system Keychain only (never `UserDefaults`,
+never logged) — see [`CLAUDE.md`](CLAUDE.md) for the relevant
+conventions if you're reviewing that code path.

SETUP.md

@@ -0,0 +1,91 @@
+# Outpost Setup Guide
+
+## Prerequisites
+
+- macOS with a recent Xcode (Xcode 16 or later)
+- A self-hosted Outline instance (or getoutline.com) and a personal API
+  key — Settings → API Keys on that instance. Outpost only ever talks
+  to Outline's public REST/WebSocket API; it doesn't vendor or run any
+  part of Outline's server.
+
+## 1. Clone with submodules
+
+The vendored OpenAPI reference (`docs/reference/outline-openapi`) is a
+git submodule.
+
+```bash
+git clone --recurse-submodules <repo-url>
+# or, if you already cloned without it:
+git submodule update --init --recursive
+```
+
+To pull that submodule up to whatever's newest upstream:
+
+```bash
+git submodule update --remote docs/reference/outline-openapi
+```
+
+## 2. Build and test `OutlineKit`
+
+`OutlineKit` is a standalone Swift package (the REST client layer) and
+the only part of this repo with a reliable command-line build/test path.
+
+```bash
+cd OutlineKit
+swift build
+swift test
+```
+
+## 3. Open the app in Xcode
+
+```bash
+open Outpost.xcodeproj
+```
+
+- Select the **Outpost** scheme.
+- In **Signing & Capabilities**, pick your own team. A free personal
+  Apple ID team works fine for building and running locally — it just
+  means the app isn't notarized, so distributed builds trigger
+  Gatekeeper's "unidentified developer" warning on other machines (see
+  `scripts/package-dmg.sh`, which ships a README explaining the bypass).
+- Run. There's no way to build the app target reliably from the CLI in
+  this project's current setup — use Xcode.
+
+## 4. Sign in
+
+On first launch, enter your Outline instance's URL and the API key
+from step 0. The token is stored in the system Keychain only.
+
+## 5. Packaging a release build
+
+After archiving in Xcode (Product → Archive → Distribute App → Copy
+App), package it into a DMG:
+
+```bash
+./scripts/package-dmg.sh /path/to/exported/Outpost.app
+```
+
+This also prints a Markdown changelog (grouped by commit type, since
+the last git tag) for pasting into release notes.
+
+## Where to go next
+
+- [`CLAUDE.md`](CLAUDE.md) — project conventions, phased build order, what's in/out of scope right now.
+- [`docs/ARCHITECTURE.md`](docs/ARCHITECTURE.md) — deeper technical rationale (API surface, the realtime collaboration transport, the CRDT engine, known risk areas).
+- [`CONTRIBUTING.md`](CONTRIBUTING.md) — branching, commit conventions, PR expectations.
+
+## Troubleshooting
+
+### `swift build`/`swift test` fails in `OutlineKit`
+Make sure you're running it from inside the `OutlineKit/` directory,
+not the repo root — it's a separate Swift package, not part of the
+Xcode project's own build.
+
+### Submodule directory is empty
+You cloned without `--recurse-submodules`. Run
+`git submodule update --init --recursive` from the repo root.
+
+### App builds but sign-in fails
+Double-check the server URL (including `https://`) and that the API
+key hasn't been revoked on the Outline instance's Settings → API Keys
+page.

scripts/package-dmg.sh

@@ -98,7 +98,12 @@ if [ -z "$LATEST_TAG" ]; then
     HEADING="Changelog"
 else
     HEAD_COMMIT="$(git -C "$REPO_ROOT" rev-parse HEAD)"
-    TAG_COMMIT="$(git -C "$REPO_ROOT" rev-parse "$LATEST_TAG")"
+    # `^{commit}` peels an annotated tag down to the commit it points at —
+    # without it, `rev-parse` on an annotated tag (e.g. `git tag -a`) returns
+    # the tag *object's* hash, which never equals a commit hash, so this
+    # comparison would always take the "not tagged yet" branch below even
+    # when HEAD genuinely is the tagged commit.
+    TAG_COMMIT="$(git -C "$REPO_ROOT" rev-parse "${LATEST_TAG}^{commit}")"
     if [ "$HEAD_COMMIT" = "$TAG_COMMIT" ]; then
         PREV_TAG="$(git -C "$REPO_ROOT" describe --tags --abbrev=0 "${LATEST_TAG}^" 2>/dev/null || true)"
         RANGE="${PREV_TAG:+$PREV_TAG..}$LATEST_TAG"