Merge pull request 'Document sharing: fix decode failures, replace broken Published toggle with real permissions' (#5) from fix/document-sharing into main

Reviewed-on: #5

.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+about: Report missing, incorrect, or outdated documentation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+        - Incorrect / outdated information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/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

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 {
-            return try await post("shares.info", body: ShareInfoRequest(documentId: documentId))
-        } catch OutlineAPIError.notFound {
-            return nil
-        }
+        // Real shape confirmed against a live server: `data` is
+        // `{ shares: [...] }`, not the bare share object the docs imply —
+        // same pattern as `pins.list`. A document could in principle have
+        // 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))
     }
@@ -230,6 +269,52 @@ 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 +371,15 @@ 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 +408,11 @@ 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/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
-/// `pins.*`. Not in the vendored OpenAPI spec (`docs/reference/outline-openapi`)
-/// — that spec has no `Pins` tag at all — but the endpoint exists on Outline's
-/// actual server (`server/routes/api/pins.ts` upstream). Shape reconstructed
-/// from general knowledge of Outline's API, not verified against this spec;
-/// treat field names as best-effort until confirmed against a live server.
+/// A document pinned to the top of a collection, or to team Home when
+/// `collectionId` is `nil`. Backed by `pins.*` — not in the vendored OpenAPI
+/// spec (`docs/reference/outline-openapi`, no `Pins` tag at all), but
+/// confirmed real against a live server's network traffic. `collectionId: nil`
+/// is what "Pin to Home" actually sends; a non-nil value is "Pin to
+/// 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 published: Bool
+    public let documentTitle: String?
+    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/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/CreatePinRequest.swift

@@ -1,6 +1,7 @@
 import Foundation
 
-/// See `OutlinePin` — best-effort shape, not in the vendored spec.
+/// See `OutlinePin`. `collectionId: nil` = "Pin to Home", non-nil = "Pin to
+/// Collection" — these are distinct actions on the real server.
 public struct CreatePinRequest: Encodable, Sendable {
     public let documentId: String
     public let collectionId: 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/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/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/UpdateDocumentRequest.swift

@@ -7,12 +7,6 @@ public struct UpdateDocumentRequest: Encodable, Sendable {
     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,
-        documentEmbeds: Bool? = nil
+        insightsEnabled: 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/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 +910,89 @@ 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 testMissingTokenThrowsTokenUnavailable() async throws {
         let httpClient = MockHTTPClient()
         let client = LiveOutlineAPIClient(

Outpost.xcodeproj/project.pbxproj

@@ -408,7 +408,7 @@
 				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 = 0.0.2;
 				PRODUCT_BUNDLE_IDENTIFIER = com.psmattas.Outpost;
 				PRODUCT_NAME = "$(TARGET_NAME)";
 				REGISTER_APP_GROUPS = YES;
@@ -453,7 +453,7 @@
 				LD_RUNPATH_SEARCH_PATHS = "@executable_path/Frameworks";
 				"LD_RUNPATH_SEARCH_PATHS[sdk=macosx*]" = "@executable_path/../Frameworks";
 				MACOSX_DEPLOYMENT_TARGET = 27.0;
-				MARKETING_VERSION = 0.0.1;
+				MARKETING_VERSION = 0.0.2;
 				PRODUCT_BUNDLE_IDENTIFIER = com.psmattas.Outpost;
 				PRODUCT_NAME = "$(TARGET_NAME)";
 				REGISTER_APP_GROUPS = YES;

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/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
-        // action — deferred rather than half-built here.
+        // DocumentShareSheet now has a real "People with access" section —
+        // 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/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 +4,10 @@ import OutlineKit
 
 struct ContentView_macOS: View {
     @Environment(SessionStore.self) private var session
+    /// 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.
@@ -12,6 +16,11 @@ 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)
@@ -43,18 +52,48 @@ 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
+        replaceDocumentPath(with: [])
+    }
 
     @ViewBuilder
     private var contextualSearchField: some View {
@@ -106,12 +145,19 @@ struct ContentView_macOS: View {
                     Image(systemName: "magnifyingglass")
                     Text("Search")
                 }
-            } else if !documentPath.isEmpty, let selectedCollection {
-                // Collection → every ancestor (icon only) → current document
-                // (icon + full title) — ancestors stay icon-only so a deep
-                // chain doesn't blow out the toolbar width.
+            } else if !documentPath.isEmpty {
+                // Origin (collection, or Home if opened from there) → every
+                // ancestor (icon only) → current document (icon + full
+                // 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 +176,11 @@ 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 +204,9 @@ struct ContentView_macOS: View {
                 apiClient: apiClient,
                 selectedCollection: $selectedCollection,
                 selectedDocumentID: documentPath.last?.id,
+                externalRefreshToken: documentsChangedToken,
+                isShowingHome: isShowingHome,
+                onSelectHome: goHome,
                 onSelectDocument: selectDocumentChain,
                 onSearchInCollection: searchInCollection
             )
@@ -205,6 +259,8 @@ 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 +285,12 @@ 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

@@ -23,6 +23,11 @@ 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 +38,22 @@ 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
     }
 
     var body: some View {
@@ -103,6 +111,9 @@ struct DocumentReaderView: View {
                     Image(systemName: "square.and.arrow.up")
                 }
                 .help("Share")
+                .popover(isPresented: $isShowingShareSheet, arrowEdge: .bottom) {
+                    DocumentShareSheet(apiClient: apiClient, documentId: viewModel.documentId)
+                }
 
                 Button {
                     Task { await viewModel.toggleEditing() }
@@ -116,7 +127,7 @@ struct DocumentReaderView: View {
                 .disabled(viewModel.isSaving)
 
                 Button {
-                    Task { await createChildDocument() }
+                    isShowingNewDocumentSheet = true
                 } label: {
                     Image(systemName: "doc.badge.plus")
                 }
@@ -127,12 +138,22 @@ 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 +218,33 @@ struct DocumentReaderView: View {
         .sheet(isPresented: $isShowingSearchSheet) {
             DocumentSearchSheet(apiClient: apiClient, document: document)
         }
-        .sheet(isPresented: $isShowingShareSheet) {
-            DocumentShareSheet(apiClient: apiClient, documentId: viewModel.documentId)
+        .sheet(isPresented: $isShowingNewDocumentSheet) {
+            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
+        ].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(
@@ -249,19 +289,22 @@ struct DocumentReaderView: View {
         Button(starStore.isStarred(documentId: viewModel.documentId) ? "Unstar" : "Star") {
             Task { await star() }
         }
-        Button(viewModel.isSubscribed ? "Unsubscribe" : "Subscribe") {
-            Task { await toggleSubscription() }
-        }
+        Toggle("Subscribed", isOn: Binding(
+            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
-        // action — deferred rather than half-built here.
-        Button("Permissions…") {}
-            .disabled(true)
+        // Membership management now lives in DocumentShareSheet's "People
+        // with access" section, alongside the share link — same sheet,
+        // same isShowingShareSheet state.
+        Button("Permissions…") {
+            isShowingShareSheet = true
+        }
 
         Divider()
 
@@ -288,9 +331,9 @@ struct DocumentReaderView: View {
         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() }
         }
 
@@ -323,15 +366,20 @@ struct DocumentReaderView: View {
 
         Divider()
 
-        Button("Enable Viewer Insights") {
-            Task { await enableInsights() }
-        }
-        Button("Enable Embeds") {
-            Task { await enableEmbeds() }
-        }
-        Button(viewModel.isFullWidth ? "Default Width" : "Full Width") {
-            Task { await toggleFullWidth() }
-        }
+        Toggle("Viewer Insights", isOn: Binding(
+            get: { viewModel.isInsightsEnabled ?? false },
+            set: { _ in Task { await toggleInsights() } }
+        ))
+        // Confirmed against a live server: there's no per-document embeds
+        // field. Only a workspace-level setting exists, and that's not
+        // 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()
 
@@ -372,19 +420,11 @@ 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.")
-        }
-    }
-
-    private func enableEmbeds() async {
-        do {
-            try await viewModel.enableEmbeds()
-        } catch {
-            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't enable embeds.")
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't update viewer insights.")
         }
     }
 
@@ -431,21 +471,6 @@ 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 {
-        share = try? await apiClient.shareInfo(documentId: documentId)
+    func loadInsightsEnabledState() async {
+        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`
-    /// in the vendored spec, so there's no state to reflect as a checkmark.
-    func enableViewerInsights() async throws {
-        _ = try await apiClient.updateDocument(UpdateDocumentRequest(id: documentId, insightsEnabled: true))
+    func toggleViewerInsights() async throws {
+        let newValue = !(isInsightsEnabled ?? false)
+        isInsightsEnabled = newValue
+        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 isUpdating = false
-    @State private var errorMessage: String?
+    @State private var titleOverride = ""
+    @State private var isLoadingShare = false
+    @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) {
-            HStack {
+        VStack(alignment: .leading, spacing: 0) {
             Text("Share")
                 .font(.headline)
-                Spacer()
-                Button("Done") { dismiss() }
+                .padding(.horizontal, 16)
+                .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 {
-                ProgressView().frame(maxWidth: .infinity)
-            } else if let errorMessage {
-                Text(errorMessage)
+    // MARK: - Link section
+
+    @ViewBuilder
+    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 {
-                    Text(share.url)
+                VStack(alignment: .leading, spacing: 6) {
+                    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)
-                .background(.fill.tertiary, in: RoundedRectangle(cornerRadius: 6))
+        .padding(.vertical, 4)
+    }
 
-                Toggle(
-                    "Published — accessible without sign-in",
-                    isOn: Binding(
-                        get: { share.published },
-                        set: { newValue in Task { await setPublished(newValue) } }
-                    )
-                )
-                .disabled(isUpdating)
-            } else {
-                Button("Create Share Link") {
-                    Task { await create() }
+    private func avatar(for name: String) -> some View {
+        Circle()
+            .fill(.fill.secondary)
+            .frame(width: 22, height: 22)
+            .overlay {
+                Text(initials(for: name))
+                    .font(.system(size: 10, weight: .semibold))
+                    .foregroundStyle(.secondary)
             }
     }
-        }
-        .padding(20)
-        .frame(width: 380)
-        .task { await load() }
+
+    private func initials(for name: String) -> String {
+        let parts = name.split(separator: " ").prefix(2)
+        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 {
-        isLoading = true
-        defer { isLoading = false }
+    private func loadShare() async {
+        isLoadingShare = true
+        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
-        defer { isLoading = false }
+        isLoadingShare = true
+        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
-        defer { isUpdating = false }
+        let trimmed = title.trimmingCharacters(in: .whitespacesAndNewlines)
+        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/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 +1,135 @@
+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 shouldn't pop the refresh banner.
+    func checkForRemoteChanges(tab: HomeTab) async {
+        async let freshPinned = fetchPinned()
+        guard let freshTab = try? await fetch(tab: tab) else { return }
+        let pinned = await freshPinned
+        if Self.fingerprint(pinned) != Self.fingerprint(pinnedDocuments)
+            || Self.fingerprint(freshTab) != Self.fingerprint(documents(for: tab)) {
+            hasRemoteChanges = true
+        }
+    }
+
+    /// `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 fetchPinned() async -> [OutlineDocument] {
+        guard let pins = try? await apiClient.listPins(ListPinsRequest(collectionId: nil)) else {
+            return []
+        }
+        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

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"