Merge pull request 'Settings parity: Profile, Preferences, Notifications, Passkeys, API & Access' (#7) from feature/settings-parity into main

Reviewed-on: #7

OutlineKit/Sources/OutlineKit/Caching/CachingOutlineAPIClient.swift

@@ -104,6 +104,27 @@ public actor CachingOutlineAPIClient: OutlineAPIClient {
 
     // MARK: - Queueable writes
 
+    /// The one exception to "no new tree structure while offline" —
+    /// synthesizes a document under a `pending-<uuid>` id (same scheme as
+    /// pin/star/subscribe), caches it so it's immediately readable/editable,
+    /// and queues the real create. On sync, the server-assigned id replaces
+    /// the placeholder in the cache; anything still referencing the old id
+    /// directly (a currently-open reader, most likely) won't follow that
+    /// rename automatically — a known, narrow limitation, not something this
+    /// pass tries to solve generally.
+    public func createDocument(_ request: CreateDocumentRequest) async throws -> OutlineDocument {
+        if !isManualOfflineModeEnabled {
+            do {
+                let result = try await live.createDocument(request)
+                await cacheDocument(result)
+                return result
+            } catch {
+                return await queueDocumentCreate(request)
+            }
+        }
+        return await queueDocumentCreate(request)
+    }
+
     public func updateDocument(_ request: UpdateDocumentRequest) async throws -> OutlineDocument {
         if !isManualOfflineModeEnabled {
             do {
@@ -214,10 +235,6 @@ public actor CachingOutlineAPIClient: OutlineAPIClient {
         try await live.searchDocumentTitles(request)
     }
 
-    public func createDocument(_ request: CreateDocumentRequest) async throws -> OutlineDocument {
-        try await live.createDocument(request)
-    }
-
     public func templatizeDocument(_ request: TemplatizeDocumentRequest) async throws -> OutlineTemplate {
         try await live.templatizeDocument(request)
     }
@@ -318,6 +335,62 @@ public actor CachingOutlineAPIClient: OutlineAPIClient {
         try await live.currentUser()
     }
 
+    public func createAttachment(_ request: CreateAttachmentRequest) async throws -> CreateAttachmentResult {
+        try await live.createAttachment(request)
+    }
+
+    public func uploadAttachmentFile(_ result: CreateAttachmentResult, fileData: Data) async throws {
+        try await live.uploadAttachmentFile(result, fileData: fileData)
+    }
+
+    public func deleteAttachment(id: String) async throws {
+        try await live.deleteAttachment(id: id)
+    }
+
+    public func updateUserAvatar(_ request: UpdateUserAvatarRequest) async throws -> OutlineUser {
+        try await live.updateUserAvatar(request)
+    }
+
+    public func updateUserName(_ request: UpdateUserNameRequest) async throws -> OutlineUser {
+        try await live.updateUserName(request)
+    }
+
+    public func updateUserLanguage(_ request: UpdateUserLanguageRequest) async throws -> OutlineUser {
+        try await live.updateUserLanguage(request)
+    }
+
+    public func updateUserPreferences(_ request: UpdateUserPreferencesRequest) async throws -> OutlineUser {
+        try await live.updateUserPreferences(request)
+    }
+
+    public func deleteAccount() async throws {
+        try await live.deleteAccount()
+    }
+
+    public func subscribeToNotifications(eventType: NotificationEventType?) async throws -> OutlineUser {
+        try await live.subscribeToNotifications(eventType: eventType)
+    }
+
+    public func unsubscribeFromNotifications(eventType: NotificationEventType?) async throws -> OutlineUser {
+        try await live.unsubscribeFromNotifications(eventType: eventType)
+    }
+
+    public func listApiKeys(_ request: ListApiKeysRequest) async throws -> [OutlineAPIKey] {
+        try await live.listApiKeys(request)
+    }
+
+    public func createApiKey(_ request: CreateApiKeyRequest) async throws -> OutlineAPIKey {
+        try await live.createApiKey(request)
+    }
+
+    public func deleteApiKey(id: String) async throws {
+        try await live.deleteApiKey(id: id)
+    }
+
+    public func installationInfo() async throws -> OutlineInstallationInfo {
+        try await live.installationInfo()
+    }
+
     // MARK: - Sync management (Settings surface)
 
     public func pendingOperations() async -> [PendingOperationSummary] {
@@ -409,6 +482,17 @@ public actor CachingOutlineAPIClient: OutlineAPIClient {
     // MARK: - Helpers
 
     private func cachedFetch<T: Codable>(key: String, fetch: () async throws -> T) async throws -> T {
+        // Manual offline mode means "skip the network entirely," not just
+        // "prefer it" — without this check, a read would still hit `live`
+        // (and succeed, showing content beyond whatever's cached) any time
+        // the device actually had a connection, defeating the point of
+        // deliberately testing/working as if offline.
+        if isManualOfflineModeEnabled {
+            if let data = await cache.load(forKey: key), let cached = try? decoder.decode(T.self, from: data) {
+                return cached
+            }
+            throw OutlineAPIError.transport(URLError(.notConnectedToInternet))
+        }
         do {
             let result = try await fetch()
             if let data = try? encoder.encode(result) {
@@ -456,6 +540,30 @@ public actor CachingOutlineAPIClient: OutlineAPIClient {
         return await cache.removeOperation(id: id)
     }
 
+    private func queueDocumentCreate(_ request: CreateDocumentRequest) async -> OutlineDocument {
+        let pendingId = "pending-\(UUID().uuidString)"
+        let now = Date()
+        let synthesized = OutlineDocument(
+            id: pendingId,
+            title: request.title,
+            text: request.text,
+            emoji: nil,
+            collectionId: request.collectionId,
+            parentDocumentId: request.parentDocumentId,
+            url: "/doc/\(pendingId)",
+            revision: nil,
+            fullWidth: nil,
+            createdAt: now,
+            updatedAt: now,
+            publishedAt: request.publish ? now : nil,
+            archivedAt: nil,
+            deletedAt: nil
+        )
+        await cacheDocument(synthesized)
+        await enqueue(.createDocument, payload: request, id: pendingId)
+        return synthesized
+    }
+
     private func queueDocumentUpdate(_ request: UpdateDocumentRequest, dueTo error: Error?) async throws -> OutlineDocument {
         guard let baseData = await cache.load(forKey: "document:\(request.id)"),
               let base = try? decoder.decode(OutlineDocument.self, from: baseData) else {
@@ -479,6 +587,26 @@ public actor CachingOutlineAPIClient: OutlineAPIClient {
             deletedAt: base.deletedAt
         )
         await cacheDocument(merged)
+
+        // Still-unsynced create for this exact document — fold the edit into
+        // the pending create's payload instead of queuing a separate update.
+        // A separate update would target `merged.id`, which is still the
+        // `pending-*` placeholder at replay time; the server has never heard
+        // of it and the update would just fail every retry.
+        if merged.id.hasPrefix("pending-"),
+           let createOp = await cache.pendingOperations().first(where: { $0.id == merged.id && $0.kind == PendingOperationKind.createDocument.rawValue }),
+           let createRequest = try? decoder.decode(CreateDocumentRequest.self, from: createOp.payload) {
+            let resolvedCreate = CreateDocumentRequest(
+                title: merged.title,
+                text: merged.text,
+                collectionId: createRequest.collectionId,
+                parentDocumentId: createRequest.parentDocumentId,
+                publish: createRequest.publish
+            )
+            await enqueue(.createDocument, payload: resolvedCreate, id: merged.id)
+            return merged
+        }
+
         // Fully resolved (not the original partial request) so replaying just
         // this one queued operation reproduces `merged` exactly — that's what
         // makes coalescing a second edit onto the same queued id safe.
@@ -538,6 +666,13 @@ public actor CachingOutlineAPIClient: OutlineAPIClient {
             ))
         }
         switch kind {
+        case .createDocument:
+            let request = try decoder.decode(CreateDocumentRequest.self, from: operation.payload)
+            let result = try await live.createDocument(request)
+            await cacheDocument(result)
+            // The placeholder id (== operation.id) is now a dead orphan —
+            // nothing server-side will ever answer to it again.
+            await cache.removeCacheEntry(forKey: "document:\(operation.id)")
         case .updateDocument:
             let request = try decoder.decode(UpdateDocumentRequest.self, from: operation.payload)
             let result = try await live.updateDocument(request)

OutlineKit/Sources/OutlineKit/Caching/OfflineCacheStore.swift

@@ -31,6 +31,16 @@ public actor OfflineCacheStore {
         return try? modelContext.fetch(descriptor).first?.payload
     }
 
+    /// Used to drop a temporary `pending-*` document's cache entry once a
+    /// queued create syncs and the server hands back the real id — the
+    /// placeholder key would otherwise sit around as a dead orphan forever.
+    public func removeCacheEntry(forKey key: String) {
+        let descriptor = FetchDescriptor<CachedPayload>(predicate: #Predicate { $0.key == key })
+        guard let existing = try? modelContext.fetch(descriptor).first else { return }
+        modelContext.delete(existing)
+        try? modelContext.save()
+    }
+
     public func itemCount() -> Int {
         (try? modelContext.fetchCount(FetchDescriptor<CachedPayload>())) ?? 0
     }

OutlineKit/Sources/OutlineKit/Caching/SyncTypes.swift

@@ -32,6 +32,7 @@ public struct FullSyncSummary: Sendable {
 /// replay later. Deliberately a small, explicit set — see its doc comment
 /// for what's excluded and why.
 enum PendingOperationKind: String, Codable, Sendable {
+    case createDocument
     case updateDocument
     case updateCollection
     case createPin

OutlineKit/Sources/OutlineKit/Core/OutlineAPIClient.swift

@@ -69,4 +69,40 @@ public protocol OutlineAPIClient: Sendable {
     func deleteStar(id: String) async throws
 
     func currentUser() async throws -> OutlineUser
+
+    /// Two-step presigned upload: this requests where/how to upload,
+    /// `uploadAttachmentFile` performs the actual multipart POST to that
+    /// target. See `OutlineAttachment`/`CreateAttachmentResult`.
+    func createAttachment(_ request: CreateAttachmentRequest) async throws -> CreateAttachmentResult
+    func uploadAttachmentFile(_ result: CreateAttachmentResult, fileData: Data) async throws
+    /// Best-effort — matches the shape every other simple `id`-only delete
+    /// in this API uses (`pins.delete`, `stars.delete`, …), not confirmed
+    /// against a live server specifically for attachments yet.
+    func deleteAttachment(id: String) async throws
+    /// `users.update`, avatar only. See `UpdateUserAvatarRequest`.
+    func updateUserAvatar(_ request: UpdateUserAvatarRequest) async throws -> OutlineUser
+    /// `users.update`, name only. See `UpdateUserNameRequest`.
+    func updateUserName(_ request: UpdateUserNameRequest) async throws -> OutlineUser
+    /// `users.update`, language only. See `UpdateUserLanguageRequest`.
+    func updateUserLanguage(_ request: UpdateUserLanguageRequest) async throws -> OutlineUser
+    /// `users.update`, preferences only. See `UpdateUserPreferencesRequest`.
+    func updateUserPreferences(_ request: UpdateUserPreferencesRequest) async throws -> OutlineUser
+    /// Backed by `users.delete` — self-service account deletion, no
+    /// confirmation code param confirmed live, matches every other simple
+    /// no-body delete in this API.
+    func deleteAccount() async throws
+    /// `nil` targets every notification event. See `NotificationEventType`.
+    func subscribeToNotifications(eventType: NotificationEventType?) async throws -> OutlineUser
+    func unsubscribeFromNotifications(eventType: NotificationEventType?) async throws -> OutlineUser
+
+    /// Settings → API & Access.
+    func listApiKeys(_ request: ListApiKeysRequest) async throws -> [OutlineAPIKey]
+    /// The returned `OutlineAPIKey.value` is the only time the full
+    /// plaintext key is ever available — the caller is responsible for
+    /// displaying it once and then discarding it.
+    func createApiKey(_ request: CreateApiKeyRequest) async throws -> OutlineAPIKey
+    func deleteApiKey(id: String) async throws
+
+    /// Settings → Installation. Self-hosted server version info.
+    func installationInfo() async throws -> OutlineInstallationInfo
 }

OutlineKit/Sources/OutlineKit/LiveOutlineAPIClient.swift

@@ -229,6 +229,103 @@ public actor LiveOutlineAPIClient: OutlineAPIClient {
         try await post("users.info", body: EmptyParams())
     }
 
+    public func createAttachment(_ request: CreateAttachmentRequest) async throws -> CreateAttachmentResult {
+        try await post("attachments.create", body: request)
+    }
+
+    /// No Bearer/CSRF header attached here, deliberately — the presigned
+    /// `form.sig` field (short-lived, scoped to this exact upload key) is
+    /// what authorizes this specific request, the same way an S3 presigned
+    /// POST works. Best-effort against a live server: if it turns out the
+    /// self-hosted local-storage backend also wants a bearer token here,
+    /// that's a one-line addition once confirmed, not a design change.
+    public func uploadAttachmentFile(_ result: CreateAttachmentResult, fileData: Data) async throws {
+        let (body, contentType) = MultipartFormDataBuilder.build(
+            fields: result.form,
+            fileFieldName: "file",
+            fileName: result.attachment.name ?? "avatar",
+            fileData: fileData,
+            fileContentType: result.form["Content-Type"] ?? "application/octet-stream"
+        )
+
+        // `uploadUrl` is a host-relative path (e.g. "/api/files.create") on
+        // a self-hosted local-storage backend, not an absolute S3 URL —
+        // resolving against `baseURL` handles both: `URL(string:relativeTo:)`
+        // replaces the whole path for a leading-slash relative string per
+        // RFC 3986, same resolution already used for user/team avatar URLs.
+        guard let uploadURL = URL(string: result.uploadUrl, relativeTo: baseURL)?.absoluteURL else {
+            throw OutlineAPIError.transport(URLError(.badURL))
+        }
+
+        var request = URLRequest(url: uploadURL)
+        request.httpMethod = "POST"
+        request.setValue(contentType, forHTTPHeaderField: "Content-Type")
+        request.httpBody = body
+
+        let data: Data
+        let response: HTTPURLResponse
+        do {
+            (data, response) = try await httpClient.send(request)
+        } catch let error as OutlineAPIError {
+            throw error
+        } catch {
+            throw OutlineAPIError.transport(error)
+        }
+
+        guard (200...299).contains(response.statusCode) else {
+            let errorEnvelope = try? decoder.decode(OutlineErrorEnvelope.self, from: data)
+            throw OutlineAPIError.server(status: response.statusCode, message: errorEnvelope?.message ?? errorEnvelope?.error)
+        }
+    }
+
+    public func deleteAttachment(id: String) async throws {
+        try await postForSuccess("attachments.delete", body: StarIDParams(id: id))
+    }
+
+    public func updateUserAvatar(_ request: UpdateUserAvatarRequest) async throws -> OutlineUser {
+        try await post("users.update", body: request)
+    }
+
+    public func updateUserName(_ request: UpdateUserNameRequest) async throws -> OutlineUser {
+        try await post("users.update", body: request)
+    }
+
+    public func updateUserLanguage(_ request: UpdateUserLanguageRequest) async throws -> OutlineUser {
+        try await post("users.update", body: request)
+    }
+
+    public func updateUserPreferences(_ request: UpdateUserPreferencesRequest) async throws -> OutlineUser {
+        try await post("users.update", body: request)
+    }
+
+    public func deleteAccount() async throws {
+        try await postForSuccess("users.delete", body: EmptyParams())
+    }
+
+    public func subscribeToNotifications(eventType: NotificationEventType?) async throws -> OutlineUser {
+        try await post("users.notificationsSubscribe", body: NotificationSubscriptionRequest(eventType: eventType?.rawValue))
+    }
+
+    public func unsubscribeFromNotifications(eventType: NotificationEventType?) async throws -> OutlineUser {
+        try await post("users.notificationsUnsubscribe", body: NotificationSubscriptionRequest(eventType: eventType?.rawValue))
+    }
+
+    public func listApiKeys(_ request: ListApiKeysRequest) async throws -> [OutlineAPIKey] {
+        try await post("apiKeys.list", body: request)
+    }
+
+    public func createApiKey(_ request: CreateApiKeyRequest) async throws -> OutlineAPIKey {
+        try await post("apiKeys.create", body: request)
+    }
+
+    public func deleteApiKey(id: String) async throws {
+        try await postForSuccess("apiKeys.delete", body: StarIDParams(id: id))
+    }
+
+    public func installationInfo() async throws -> OutlineInstallationInfo {
+        try await post("installation.info", body: EmptyParams())
+    }
+
     private func post<Body: Encodable, Response: Decodable>(_ path: String, body: Body) async throws -> Response {
         guard let token = try? tokenStore.token() else {
             throw OutlineAPIError.tokenUnavailable

OutlineKit/Sources/OutlineKit/Models/NotificationEventType.swift

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

OutlineKit/Sources/OutlineKit/Models/OutlineAPIKey.swift

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

OutlineKit/Sources/OutlineKit/Models/OutlineAttachment.swift

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

OutlineKit/Sources/OutlineKit/Models/OutlineInstallationInfo.swift

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

OutlineKit/Sources/OutlineKit/Models/OutlineUser.swift

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

OutlineKit/Sources/OutlineKit/Models/OutlineUserPreferences.swift

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

OutlineKit/Sources/OutlineKit/Networking/MultipartFormDataBuilder.swift

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

OutlineKit/Sources/OutlineKit/Requests/CreateApiKeyRequest.swift

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

OutlineKit/Sources/OutlineKit/Requests/CreateAttachmentRequest.swift

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

OutlineKit/Sources/OutlineKit/Requests/CreateDocumentRequest.swift

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

OutlineKit/Sources/OutlineKit/Requests/ListApiKeysRequest.swift

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

OutlineKit/Sources/OutlineKit/Requests/NotificationSubscriptionRequest.swift

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

OutlineKit/Sources/OutlineKit/Requests/UpdateUserAvatarRequest.swift

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

OutlineKit/Sources/OutlineKit/Requests/UpdateUserLanguageRequest.swift

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

OutlineKit/Sources/OutlineKit/Requests/UpdateUserNameRequest.swift

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

OutlineKit/Sources/OutlineKit/Requests/UpdateUserPreferencesRequest.swift

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

OutlineKit/Tests/OutlineKitTests/CachingOutlineAPIClientTests.swift

@@ -13,6 +13,7 @@ private final class StubOutlineAPIClient: OutlineAPIClient, @unchecked Sendable
     var createPinHandler: (@Sendable (CreatePinRequest) async throws -> OutlinePin)?
     var deletePinHandler: (@Sendable (String) async throws -> Void)?
     var listDocumentsHandler: (@Sendable (String?, String?, Int, Int) async throws -> [OutlineDocument])?
+    var createDocumentHandler: (@Sendable (CreateDocumentRequest) async throws -> OutlineDocument)?
 
     func authInfo() async throws -> OutlineAuthInfo { throw NotStubbed() }
 
@@ -30,7 +31,10 @@ private final class StubOutlineAPIClient: OutlineAPIClient, @unchecked Sendable
     func listViewedDocuments(offset: Int, limit: Int) async throws -> [OutlineDocument] { throw NotStubbed() }
     func searchDocuments(_ request: DocumentSearchRequest) async throws -> [OutlineDocumentSearchResult] { throw NotStubbed() }
     func searchDocumentTitles(_ request: DocumentSearchTitlesRequest) async throws -> [OutlineDocument] { throw NotStubbed() }
-    func createDocument(_ request: CreateDocumentRequest) async throws -> OutlineDocument { throw NotStubbed() }
+    func createDocument(_ request: CreateDocumentRequest) async throws -> OutlineDocument {
+        guard let handler = createDocumentHandler else { throw NotStubbed() }
+        return try await handler(request)
+    }
 
     func updateDocument(_ request: UpdateDocumentRequest) async throws -> OutlineDocument {
         guard let handler = updateDocumentHandler else { throw NotStubbed() }
@@ -85,6 +89,20 @@ private final class StubOutlineAPIClient: OutlineAPIClient, @unchecked Sendable
     func listStars(_ request: ListStarsRequest) async throws -> [OutlineStar] { throw NotStubbed() }
     func deleteStar(id: String) async throws { throw NotStubbed() }
     func currentUser() async throws -> OutlineUser { throw NotStubbed() }
+    func createAttachment(_ request: CreateAttachmentRequest) async throws -> CreateAttachmentResult { throw NotStubbed() }
+    func uploadAttachmentFile(_ result: CreateAttachmentResult, fileData: Data) async throws { throw NotStubbed() }
+    func deleteAttachment(id: String) async throws { throw NotStubbed() }
+    func updateUserAvatar(_ request: UpdateUserAvatarRequest) async throws -> OutlineUser { throw NotStubbed() }
+    func updateUserName(_ request: UpdateUserNameRequest) async throws -> OutlineUser { throw NotStubbed() }
+    func updateUserLanguage(_ request: UpdateUserLanguageRequest) async throws -> OutlineUser { throw NotStubbed() }
+    func updateUserPreferences(_ request: UpdateUserPreferencesRequest) async throws -> OutlineUser { throw NotStubbed() }
+    func deleteAccount() async throws { throw NotStubbed() }
+    func subscribeToNotifications(eventType: NotificationEventType?) async throws -> OutlineUser { throw NotStubbed() }
+    func unsubscribeFromNotifications(eventType: NotificationEventType?) async throws -> OutlineUser { throw NotStubbed() }
+    func listApiKeys(_ request: ListApiKeysRequest) async throws -> [OutlineAPIKey] { throw NotStubbed() }
+    func createApiKey(_ request: CreateApiKeyRequest) async throws -> OutlineAPIKey { throw NotStubbed() }
+    func deleteApiKey(id: String) async throws { throw NotStubbed() }
+    func installationInfo() async throws -> OutlineInstallationInfo { throw NotStubbed() }
 }
 
 private struct StubTransportError: Error {}
@@ -326,6 +344,39 @@ final class CachingOutlineAPIClientTests: XCTestCase {
         XCTAssertTrue(pin.id.hasPrefix("pending-"))
     }
 
+    /// Regression test: manual offline mode used to only gate writes —
+    /// reads (listCollections, documentInfo, etc.) still hit `live` first
+    /// any time the device actually had a connection, silently defeating
+    /// "skip the network entirely" for the one thing that mattered most:
+    /// the sidebar showing more than what was actually cached.
+    func testManualOfflineModeSkipsLiveForReadsToo() async throws {
+        let defaults = UserDefaults(suiteName: "CachingOutlineAPIClientTests.manualOfflineReads")!
+        defaults.removePersistentDomain(forName: "CachingOutlineAPIClientTests.manualOfflineReads")
+
+        let stub = StubOutlineAPIClient()
+        let cachedCollection = makeCollection(id: "col-1")
+        var liveCallCount = 0
+        stub.listCollectionsHandler = { _, _ in
+            liveCallCount += 1
+            return [cachedCollection]
+        }
+        let cache = try makeCache()
+        let sut = CachingOutlineAPIClient(live: stub, cache: cache, defaults: defaults)
+
+        // Online first — populates the cache normally.
+        let firstResult = try await sut.listCollections(offset: 0, limit: 25)
+        XCTAssertEqual(firstResult, [cachedCollection])
+        XCTAssertEqual(liveCallCount, 1)
+
+        // Flip manual offline mode on, still "connected" (stub would happily
+        // answer) — the live call must not be attempted at all.
+        defaults.set(true, forKey: CachingOutlineAPIClient.offlineModeDefaultsKey)
+        let secondResult = try await sut.listCollections(offset: 0, limit: 25)
+
+        XCTAssertEqual(secondResult, [cachedCollection])
+        XCTAssertEqual(liveCallCount, 1, "listCollections should have served entirely from cache")
+    }
+
     func testCacheStorageSummaryReflectsCachedItems() async throws {
         let stub = StubOutlineAPIClient()
         stub.documentInfoHandler = { _ in self.makeDocument() }
@@ -385,4 +436,79 @@ final class CachingOutlineAPIClientTests: XCTestCase {
         let cachedDoc = try await sut.documentInfo(id: "doc-2")
         XCTAssertEqual(cachedDoc.id, "doc-2")
     }
+
+    // MARK: - Offline document creation
+
+    func testCreateDocumentQueuesAndReturnsUsableDocumentWhenOffline() async throws {
+        let stub = StubOutlineAPIClient()
+        stub.createDocumentHandler = { _ in throw StubTransportError() }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        let created = try await sut.createDocument(
+            CreateDocumentRequest(title: "New Doc", text: "hello", collectionId: "col-1")
+        )
+
+        XCTAssertTrue(created.id.hasPrefix("pending-"))
+        XCTAssertEqual(created.title, "New Doc")
+        XCTAssertEqual(created.text, "hello")
+
+        // It's immediately readable, same as any other cached document.
+        stub.documentInfoHandler = { _ in throw StubTransportError() }
+        let reopened = try await sut.documentInfo(id: created.id)
+        XCTAssertEqual(reopened.title, "New Doc")
+
+        let pending = await sut.pendingOperations()
+        XCTAssertEqual(pending.count, 1)
+        XCTAssertEqual(pending.first?.kind, "createDocument")
+    }
+
+    func testEditingAnUnsyncedCreatedDocumentFoldsIntoTheCreateInsteadOfQueuingAnUpdate() async throws {
+        let stub = StubOutlineAPIClient()
+        stub.createDocumentHandler = { _ in throw StubTransportError() }
+        stub.updateDocumentHandler = { _ in throw StubTransportError() }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        let created = try await sut.createDocument(
+            CreateDocumentRequest(title: "Untitled", text: "", collectionId: "col-1")
+        )
+        _ = try await sut.updateDocument(UpdateDocumentRequest(id: created.id, title: "Real Title", text: "Real body"))
+
+        let pending = await sut.pendingOperations()
+        XCTAssertEqual(pending.count, 1, "the edit should have folded into the pending create, not added a second operation")
+        XCTAssertEqual(pending.first?.kind, "createDocument")
+
+        stub.documentInfoHandler = { _ in throw StubTransportError() }
+        let reopened = try await sut.documentInfo(id: created.id)
+        XCTAssertEqual(reopened.title, "Real Title")
+        XCTAssertEqual(reopened.text, "Real body")
+    }
+
+    func testFlushingAPendingCreateReconcilesThePlaceholderIdToTheRealOne() async throws {
+        let stub = StubOutlineAPIClient()
+        stub.createDocumentHandler = { _ in throw StubTransportError() }
+        let sut = CachingOutlineAPIClient(live: stub, cache: try makeCache())
+
+        let created = try await sut.createDocument(
+            CreateDocumentRequest(title: "New Doc", text: "hello", collectionId: "col-1")
+        )
+        let realDocument = makeDocument(id: "real-server-id", title: "New Doc")
+        stub.createDocumentHandler = { _ in realDocument }
+
+        let summary = await sut.flushPendingOperations()
+        XCTAssertEqual(summary.succeeded, 1)
+        XCTAssertEqual(summary.failed, 0)
+
+        // The real document is now readable under its real id...
+        stub.documentInfoHandler = { _ in throw StubTransportError() }
+        let byRealId = try await sut.documentInfo(id: "real-server-id")
+        XCTAssertEqual(byRealId.id, "real-server-id")
+
+        // ...and the placeholder is gone rather than left as a dead orphan.
+        do {
+            _ = try await sut.documentInfo(id: created.id)
+            XCTFail("Expected the placeholder cache entry to have been removed")
+        } catch {
+            // expected — nothing left under the old id
+        }
+    }
 }

OutlineKit/Tests/OutlineKitTests/LiveOutlineAPIClientTests.swift

@@ -993,6 +993,490 @@ final class LiveOutlineAPIClientTests: XCTestCase {
         XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/users.list")
     }
 
+    func testUpdateUserAvatarSendsExplicitNullWhenRemoving() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "user-1",
+                "name": "Jane Doe",
+                "avatarUrl": null
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let user = try await client.updateUserAvatar(UpdateUserAvatarRequest(id: "user-1", avatarUrl: nil))
+
+        XCTAssertNil(user.avatarUrl)
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/users.update")
+        let sentBody = try XCTUnwrap(httpClient.lastRequest?.httpBody)
+        let sentJSON = try XCTUnwrap(String(data: sentBody, encoding: .utf8))
+        // The whole point of UpdateUserAvatarRequest's custom encode(to:) —
+        // Swift's synthesized Encodable would have omitted the key entirely
+        // for a nil Optional instead of sending a literal null.
+        XCTAssertTrue(sentJSON.contains("\"avatarUrl\":null"), "expected an explicit null, got: \(sentJSON)")
+    }
+
+    func testUpdateUserAvatarSendsTheNewURLWhenSet() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "user-1",
+                "name": "Jane Doe",
+                "avatarUrl": "/api/attachments.redirect?id=abc"
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let user = try await client.updateUserAvatar(
+            UpdateUserAvatarRequest(id: "user-1", avatarUrl: "/api/attachments.redirect?id=abc")
+        )
+
+        XCTAssertEqual(user.avatarUrl, "/api/attachments.redirect?id=abc")
+        let sentBody = try XCTUnwrap(httpClient.lastRequest?.httpBody)
+        let sentJSON = try XCTUnwrap(String(data: sentBody, encoding: .utf8))
+        XCTAssertTrue(sentJSON.contains("\"id\":\"user-1\""))
+    }
+
+    func testUpdateUserNameSendsRequestAndDecodesResult() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "user-1",
+                "name": "New Name"
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let user = try await client.updateUserName(UpdateUserNameRequest(id: "user-1", name: "New Name"))
+
+        XCTAssertEqual(user.name, "New Name")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/users.update")
+    }
+
+    func testUpdateUserLanguageSendsRequestAndDecodesResult() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "user-1",
+                "name": "Jane Doe",
+                "language": "fr_FR"
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let user = try await client.updateUserLanguage(UpdateUserLanguageRequest(id: "user-1", language: "fr_FR"))
+
+        XCTAssertEqual(user.language, "fr_FR")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/users.update")
+    }
+
+    func testUpdateUserPreferencesSendsWholeObjectAndDecodesResult() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "user-1",
+                "name": "Jane Doe",
+                "preferences": { "rememberLastPath": true, "useCursorPointer": true }
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let preferences = OutlineUserPreferences(rememberLastPath: true, useCursorPointer: true)
+        let user = try await client.updateUserPreferences(UpdateUserPreferencesRequest(id: "user-1", preferences: preferences))
+
+        XCTAssertEqual(user.preferences?.rememberLastPath, true)
+        XCTAssertEqual(user.preferences?.useCursorPointer, true)
+
+        let sentBody = try JSONSerialization.jsonObject(with: httpClient.lastRequest!.httpBody!) as? [String: Any]
+        let sentPreferences = sentBody?["preferences"] as? [String: Any]
+        XCTAssertEqual(sentPreferences?["rememberLastPath"] as? Bool, true)
+        XCTAssertEqual(sentPreferences?["useCursorPointer"] as? Bool, true)
+    }
+
+    /// Locks in the wire mapping confirmed against a live server's own web
+    /// app traffic: `seamlessEdit`/`commentsInGutter`/`enableSmartText` are
+    /// the real keys (not `separateEditing`/`showCommentMarker`/`smartText`
+    /// this struct exposes), and `seamlessEdit` is the *negation* of this
+    /// app's `separateEditing`.
+    func testOutlineUserPreferencesDecodesRealWireKeys() throws {
+        let json = """
+        {
+            "seamlessEdit": false,
+            "commentsInGutter": true,
+            "enableSmartText": true,
+            "rememberLastPath": true,
+            "useCursorPointer": true,
+            "codeBlockLineNumbers": false,
+            "notificationBadge": "indicator",
+            "fullWidthDocuments": true
+        }
+        """.data(using: .utf8)!
+
+        let preferences = try JSONDecoder().decode(OutlineUserPreferences.self, from: json)
+
+        XCTAssertEqual(preferences.separateEditing, true, "seamlessEdit: false means separate editing is ON")
+        XCTAssertEqual(preferences.showCommentMarker, true)
+        XCTAssertEqual(preferences.smartText, true)
+        XCTAssertEqual(preferences.rememberLastPath, true)
+        XCTAssertEqual(preferences.useCursorPointer, true)
+        XCTAssertEqual(preferences.codeBlockLineNumbers, false)
+        XCTAssertEqual(preferences.notificationBadge, "indicator")
+        XCTAssertEqual(preferences.fullWidthDocuments, true)
+    }
+
+    func testOutlineUserPreferencesEncodesRealWireKeysAndInvertsSeparateEditing() throws {
+        var preferences = OutlineUserPreferences()
+        preferences.separateEditing = true
+        preferences.showCommentMarker = false
+        preferences.smartText = true
+        preferences.fullWidthDocuments = true
+
+        let data = try JSONEncoder().encode(preferences)
+        let object = try JSONSerialization.jsonObject(with: data) as? [String: Any]
+
+        XCTAssertEqual(object?["seamlessEdit"] as? Bool, false, "separateEditing: true must encode as seamlessEdit: false")
+        XCTAssertEqual(object?["commentsInGutter"] as? Bool, false)
+        XCTAssertEqual(object?["enableSmartText"] as? Bool, true)
+        XCTAssertEqual(object?["fullWidthDocuments"] as? Bool, true)
+        XCTAssertNil(object?["separateEditing"], "must not leak this app's own field name onto the wire")
+        XCTAssertNil(object?["showCommentMarker"])
+        XCTAssertNil(object?["smartText"])
+    }
+
+    func testSubscribeToNotificationsSendsEventTypeAndDecodesResult() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "user-1",
+                "name": "Jane Doe",
+                "notificationSettings": { "documents.publish": true }
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let user = try await client.subscribeToNotifications(eventType: .documentPublish)
+
+        XCTAssertEqual(user.notificationSettings?["documents.publish"], true)
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/users.notificationsSubscribe")
+        let sentBody = try JSONSerialization.jsonObject(with: httpClient.lastRequest!.httpBody!) as? [String: Any]
+        XCTAssertEqual(sentBody?["eventType"] as? String, "documents.publish")
+    }
+
+    func testUnsubscribeFromNotificationsWithNilEventTypeTargetsAll() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "user-1",
+                "name": "Jane Doe",
+                "notificationSettings": { "documents.publish": false }
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        _ = try await client.unsubscribeFromNotifications(eventType: nil)
+
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/users.notificationsUnsubscribe")
+        let sentBody = try JSONSerialization.jsonObject(with: httpClient.lastRequest!.httpBody!) as? [String: Any]
+        XCTAssertNil(sentBody?["eventType"])
+    }
+
+    func testListApiKeysDecodesResult() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "pagination": { "limit": 25, "offset": 0 },
+            "data": [
+                {
+                    "id": "c3eec545-6d38-4065-90dc-b6c96a551445",
+                    "name": "Outpost",
+                    "scope": null,
+                    "last4": "dl1h",
+                    "createdAt": "2026-08-12T18:44:32.467Z",
+                    "updatedAt": "2026-08-12T18:44:32.467Z",
+                    "expiresAt": null,
+                    "lastActiveAt": "2026-08-18T01:01:36.553Z"
+                }
+            ]
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let keys = try await client.listApiKeys(ListApiKeysRequest())
+
+        XCTAssertEqual(keys.count, 1)
+        XCTAssertEqual(keys.first?.name, "Outpost")
+        XCTAssertEqual(keys.first?.last4, "dl1h")
+        XCTAssertNil(keys.first?.expiresAt)
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/apiKeys.list")
+    }
+
+    func testInstallationInfoDecodesResult() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": { "version": "1.9.2", "latestVersion": "1.9.2", "versionsBehind": 0 },
+            "policies": []
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let info = try await client.installationInfo()
+
+        XCTAssertEqual(info.version, "1.9.2")
+        XCTAssertEqual(info.versionsBehind, 0)
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/installation.info")
+    }
+
+    func testCreateApiKeyOmitsExpiresAtWhenNilAndDecodesValue() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "5655fb3e-2a8c-4f2c-9cae-bbd910ef8683",
+                "name": "test",
+                "scope": null,
+                "value": "ol_api_Xqx9Jti7xUunb5b8bXh29vHmBngqjJl3Id0DGv",
+                "last4": "0DGv",
+                "createdAt": "2026-08-18T15:39:29.872Z",
+                "expiresAt": null,
+                "lastActiveAt": null
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let key = try await client.createApiKey(CreateApiKeyRequest(name: "test"))
+
+        XCTAssertEqual(key.value, "ol_api_Xqx9Jti7xUunb5b8bXh29vHmBngqjJl3Id0DGv")
+        XCTAssertNil(key.expiresAt)
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/apiKeys.create")
+        let sentBody = try JSONSerialization.jsonObject(with: httpClient.lastRequest!.httpBody!) as? [String: Any]
+        XCTAssertEqual(sentBody?["name"] as? String, "test")
+        XCTAssertNil(sentBody?["expiresAt"], "omitting expiresAt (not sending null) is what produces a non-expiring key")
+        XCTAssertNil(sentBody?["scope"])
+    }
+
+    func testCreateApiKeySendsExpiresAtWhenProvided() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "04e204fb-51a4-4b54-aed1-2056dfd576d7",
+                "name": "Test",
+                "scope": null,
+                "value": "ol_api_aeYcOts7I2sJXw3zaztjydRM3W3W89TBAtcLts",
+                "last4": "cLts",
+                "createdAt": "2026-08-18T15:38:22.928Z",
+                "expiresAt": "2026-11-16T23:59:59.999Z",
+                "lastActiveAt": null
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let expiresAt = Date(timeIntervalSince1970: 1_795_000_000)
+        _ = try await client.createApiKey(CreateApiKeyRequest(name: "Test", expiresAt: expiresAt))
+
+        let sentBody = try JSONSerialization.jsonObject(with: httpClient.lastRequest!.httpBody!) as? [String: Any]
+        XCTAssertNotNil(sentBody?["expiresAt"])
+    }
+
+    func testDeleteApiKeySendsRequest() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "success": true }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        try await client.deleteApiKey(id: "5655fb3e-2a8c-4f2c-9cae-bbd910ef8683")
+
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/apiKeys.delete")
+        let sentBody = try JSONSerialization.jsonObject(with: httpClient.lastRequest!.httpBody!) as? [String: Any]
+        XCTAssertEqual(sentBody?["id"] as? String, "5655fb3e-2a8c-4f2c-9cae-bbd910ef8683")
+    }
+
+    func testDeleteAccountSendsRequest() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "success": true }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        try await client.deleteAccount()
+
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/users.delete")
+    }
+
+    func testDeleteAttachmentSendsRequest() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "success": true }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        try await client.deleteAttachment(id: "attach-1")
+
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/attachments.delete")
+    }
+
+    func testCreateAttachmentDecodesUploadTargetAndFormFields() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "attachment": {
+                    "id": "attach-1",
+                    "documentId": null,
+                    "contentType": "image/jpeg",
+                    "name": "avatar.jpg",
+                    "url": "/api/attachments.redirect?id=attach-1",
+                    "size": "59304"
+                },
+                "uploadUrl": "/api/files.create",
+                "form": {
+                    "Content-Type": "image/jpeg",
+                    "key": "uploads/user-1/attach-1/avatar.jpg",
+                    "acl": "public-read"
+                }
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let result = try await client.createAttachment(
+            CreateAttachmentRequest(name: "avatar.jpg", contentType: "image/jpeg", size: 59304)
+        )
+
+        XCTAssertEqual(result.attachment.id, "attach-1")
+        XCTAssertEqual(result.attachment.size, "59304")
+        XCTAssertEqual(result.uploadUrl, "/api/files.create")
+        XCTAssertEqual(result.form["acl"], "public-read")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/attachments.create")
+    }
+
+    func testUploadAttachmentFilePostsToTheResolvedRelativeURL() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "success": true }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let uploadTarget = CreateAttachmentResult(
+            attachment: OutlineAttachment(
+                id: "attach-1",
+                documentId: nil,
+                contentType: "image/jpeg",
+                name: "avatar.jpg",
+                url: "/api/attachments.redirect?id=attach-1",
+                size: "3"
+            ),
+            uploadUrl: "/api/files.create",
+            form: ["Content-Type": "image/jpeg", "key": "uploads/attach-1"]
+        )
+
+        try await client.uploadAttachmentFile(uploadTarget, fileData: Data("abc".utf8))
+
+        // Resolved against baseURL's host, not appended onto "/api/<baseURL-relative-path>".
+        XCTAssertEqual(httpClient.lastRequest?.url?.absoluteString, "https://outline.example.com/api/files.create")
+        XCTAssertNil(httpClient.lastRequest?.value(forHTTPHeaderField: "Authorization"))
+        let contentType = httpClient.lastRequest?.value(forHTTPHeaderField: "Content-Type")
+        XCTAssertTrue(contentType?.hasPrefix("multipart/form-data; boundary=") ?? false)
+    }
+
     func testMissingTokenThrowsTokenUnavailable() async throws {
         let httpClient = MockHTTPClient()
         let client = LiveOutlineAPIClient(

OutlineKit/Tests/OutlineKitTests/MultipartFormDataBuilderTests.swift

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

Outpost.xcodeproj/project.pbxproj

@@ -299,7 +299,7 @@
 				CLANG_WARN__DUPLICATE_METHOD_MATCH = YES;
 				COPY_PHASE_STRIP = NO;
 				DEBUG_INFORMATION_FORMAT = dwarf;
-				DEVELOPMENT_TEAM = B95H74ZDY6;
+				DEVELOPMENT_TEAM = CW6GQT9SK5;
 				ENABLE_STRICT_OBJC_MSGSEND = YES;
 				ENABLE_TESTABILITY = YES;
 				ENABLE_USER_SCRIPT_SANDBOXING = YES;
@@ -361,7 +361,7 @@
 				CLANG_WARN__DUPLICATE_METHOD_MATCH = YES;
 				COPY_PHASE_STRIP = NO;
 				DEBUG_INFORMATION_FORMAT = "dwarf-with-dsym";
-				DEVELOPMENT_TEAM = B95H74ZDY6;
+				DEVELOPMENT_TEAM = CW6GQT9SK5;
 				ENABLE_NS_ASSERTIONS = NO;
 				ENABLE_STRICT_OBJC_MSGSEND = YES;
 				ENABLE_USER_SCRIPT_SANDBOXING = YES;
@@ -385,15 +385,20 @@
 			buildSettings = {
 				ASSETCATALOG_COMPILER_APPICON_NAME = AppIcon;
 				ASSETCATALOG_COMPILER_GLOBAL_ACCENT_COLOR_NAME = AccentColor;
+				ASSETCATALOG_COMPILER_INCLUDE_ALL_APPICON_ASSETS = YES;
 				CODE_SIGN_ENTITLEMENTS = Outpost/Outpost.entitlements;
+				CODE_SIGN_IDENTITY = "Apple Development";
+				"CODE_SIGN_IDENTITY[sdk=macosx*]" = "Apple Development";
 				CODE_SIGN_STYLE = Automatic;
 				CURRENT_PROJECT_VERSION = 1;
-				DEVELOPMENT_TEAM = B95H74ZDY6;
+				DEVELOPMENT_TEAM = CW6GQT9SK5;
 				ENABLE_APP_SANDBOX = YES;
 				ENABLE_HARDENED_RUNTIME = YES;
 				ENABLE_PREVIEWS = YES;
 				ENABLE_USER_SELECTED_FILES = readonly;
 				GENERATE_INFOPLIST_FILE = YES;
+				INFOPLIST_KEY_CFBundleDisplayName = Outpost;
+				INFOPLIST_KEY_LSApplicationCategoryType = "public.app-category.productivity";
 				"INFOPLIST_KEY_UIApplicationSceneManifest_Generation[sdk=iphoneos*]" = YES;
 				"INFOPLIST_KEY_UIApplicationSceneManifest_Generation[sdk=iphonesimulator*]" = YES;
 				"INFOPLIST_KEY_UIApplicationSupportsIndirectInputEvents[sdk=iphoneos*]" = YES;
@@ -408,9 +413,10 @@
 				LD_RUNPATH_SEARCH_PATHS = "@executable_path/Frameworks";
 				"LD_RUNPATH_SEARCH_PATHS[sdk=macosx*]" = "@executable_path/../Frameworks";
 				MACOSX_DEPLOYMENT_TARGET = 27.0;
-				MARKETING_VERSION = 0.0.2;
+				MARKETING_VERSION = 0.0.4;
-				PRODUCT_BUNDLE_IDENTIFIER = com.psmattas.Outpost;
+				PRODUCT_BUNDLE_IDENTIFIER = com.psmattas.OutpostApp;
 				PRODUCT_NAME = "$(TARGET_NAME)";
+				PROVISIONING_PROFILE_SPECIFIER = "";
 				REGISTER_APP_GROUPS = YES;
 				SDKROOT = auto;
 				STRING_CATALOG_GENERATE_SYMBOLS = YES;
@@ -430,15 +436,20 @@
 			buildSettings = {
 				ASSETCATALOG_COMPILER_APPICON_NAME = AppIcon;
 				ASSETCATALOG_COMPILER_GLOBAL_ACCENT_COLOR_NAME = AccentColor;
+				ASSETCATALOG_COMPILER_INCLUDE_ALL_APPICON_ASSETS = YES;
 				CODE_SIGN_ENTITLEMENTS = Outpost/Outpost.entitlements;
+				CODE_SIGN_IDENTITY = "Apple Development";
+				"CODE_SIGN_IDENTITY[sdk=macosx*]" = "Apple Development";
 				CODE_SIGN_STYLE = Automatic;
 				CURRENT_PROJECT_VERSION = 1;
-				DEVELOPMENT_TEAM = B95H74ZDY6;
+				DEVELOPMENT_TEAM = CW6GQT9SK5;
 				ENABLE_APP_SANDBOX = YES;
 				ENABLE_HARDENED_RUNTIME = YES;
 				ENABLE_PREVIEWS = YES;
 				ENABLE_USER_SELECTED_FILES = readonly;
 				GENERATE_INFOPLIST_FILE = YES;
+				INFOPLIST_KEY_CFBundleDisplayName = Outpost;
+				INFOPLIST_KEY_LSApplicationCategoryType = "public.app-category.productivity";
 				"INFOPLIST_KEY_UIApplicationSceneManifest_Generation[sdk=iphoneos*]" = YES;
 				"INFOPLIST_KEY_UIApplicationSceneManifest_Generation[sdk=iphonesimulator*]" = YES;
 				"INFOPLIST_KEY_UIApplicationSupportsIndirectInputEvents[sdk=iphoneos*]" = YES;
@@ -453,9 +464,10 @@
 				LD_RUNPATH_SEARCH_PATHS = "@executable_path/Frameworks";
 				"LD_RUNPATH_SEARCH_PATHS[sdk=macosx*]" = "@executable_path/../Frameworks";
 				MACOSX_DEPLOYMENT_TARGET = 27.0;
-				MARKETING_VERSION = 0.0.2;
+				MARKETING_VERSION = 0.0.4;
-				PRODUCT_BUNDLE_IDENTIFIER = com.psmattas.Outpost;
+				PRODUCT_BUNDLE_IDENTIFIER = com.psmattas.OutpostApp;
 				PRODUCT_NAME = "$(TARGET_NAME)";
+				PROVISIONING_PROFILE_SPECIFIER = "";
 				REGISTER_APP_GROUPS = YES;
 				SDKROOT = auto;
 				STRING_CATALOG_GENERATE_SYMBOLS = YES;
@@ -476,7 +488,7 @@
 				BUNDLE_LOADER = "$(TEST_HOST)";
 				CODE_SIGN_STYLE = Automatic;
 				CURRENT_PROJECT_VERSION = 1;
-				DEVELOPMENT_TEAM = B95H74ZDY6;
+				DEVELOPMENT_TEAM = CW6GQT9SK5;
 				GENERATE_INFOPLIST_FILE = YES;
 				IPHONEOS_DEPLOYMENT_TARGET = 27.0;
 				MACOSX_DEPLOYMENT_TARGET = 27.0;
@@ -502,7 +514,7 @@
 				BUNDLE_LOADER = "$(TEST_HOST)";
 				CODE_SIGN_STYLE = Automatic;
 				CURRENT_PROJECT_VERSION = 1;
-				DEVELOPMENT_TEAM = B95H74ZDY6;
+				DEVELOPMENT_TEAM = CW6GQT9SK5;
 				GENERATE_INFOPLIST_FILE = YES;
 				IPHONEOS_DEPLOYMENT_TARGET = 27.0;
 				MACOSX_DEPLOYMENT_TARGET = 27.0;
@@ -527,7 +539,7 @@
 			buildSettings = {
 				CODE_SIGN_STYLE = Automatic;
 				CURRENT_PROJECT_VERSION = 1;
-				DEVELOPMENT_TEAM = B95H74ZDY6;
+				DEVELOPMENT_TEAM = CW6GQT9SK5;
 				GENERATE_INFOPLIST_FILE = YES;
 				IPHONEOS_DEPLOYMENT_TARGET = 27.0;
 				MACOSX_DEPLOYMENT_TARGET = 27.0;
@@ -552,7 +564,7 @@
 			buildSettings = {
 				CODE_SIGN_STYLE = Automatic;
 				CURRENT_PROJECT_VERSION = 1;
-				DEVELOPMENT_TEAM = B95H74ZDY6;
+				DEVELOPMENT_TEAM = CW6GQT9SK5;
 				GENERATE_INFOPLIST_FILE = YES;
 				IPHONEOS_DEPLOYMENT_TARGET = 27.0;
 				MACOSX_DEPLOYMENT_TARGET = 27.0;

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

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

Outpost/Features/About/AboutView.swift

@@ -14,17 +14,7 @@ struct AboutInfoView: View {
         Bundle.main.object(forInfoDictionaryKey: "CFBundleName") as? String ?? "Outpost"
     }
 
-    /// Bumped alongside `MARKETING_VERSION` in the Xcode project — kept out
+    var versionString: String { OutpostVersion.fullVersionString }
-    /// of the bundle version itself since `CFBundleShortVersionString` is
-    /// expected to stay a plain dotted-numeric string, not `0.0.1-ALPHA`.
-    private let releaseStage = "ALPHA"
-
-    var versionString: String {
-        let shortVersion = Bundle.main.object(forInfoDictionaryKey: "CFBundleShortVersionString") as? String ?? "0.0.1"
-        let buildNumber = Bundle.main.object(forInfoDictionaryKey: "CFBundleVersion") as? String ?? "1"
-        let stageSuffix = releaseStage.isEmpty ? "" : "-\(releaseStage)"
-        return "Version \(shortVersion)\(stageSuffix) (\(buildNumber))"
-    }
 
     private var copyrightYear: String {
         String(Calendar.current.component(.year, from: Date()))

Outpost/Features/Account/AvatarCropperView.swift

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

Outpost/Features/Account/SettingsSidebarList.swift

@@ -1,15 +1,34 @@
 #if os(macOS)
 import SwiftUI
+import OutlineKit
 
 /// Swapped into the real sidebar's content slot (search field, collections
 /// tree, account footer) while Settings is open — same sidebar, different
 /// content, rather than a separate mini sidebar nested inside a page. "Done"
 /// clears `AppNavigation.isShowingSettings`, which puts the collections tree
 /// back.
+///
+/// Grouped by `SettingsCategory` — `general` (ours) sits under an "Outpost"
+/// header at the top, then Outline's own Account/Workspace groups, matching
+/// the settings page structure of the Outline web app. Outline's own server
+/// version has no dedicated section (there used to be an Integrations &
+/// Installation category for just that) — it's cheap enough to show
+/// unconditionally in the footer here instead, alongside Outpost's own
+/// version.
 struct SettingsSidebarList: View {
     @Binding var selection: SettingsSection?
     let onDone: () -> Void
 
+    @Environment(SessionStore.self) private var session
+    @AppStorage(CachingOutlineAPIClient.offlineModeDefaultsKey) private var isOfflineModeEnabled = false
+    @State private var outlineVersion: String?
+
+    /// Mirrors `SettingsView`'s own check — a real dropped connection or
+    /// the manual Offline Mode toggle both mean there's no server to ask.
+    private var isEffectivelyOnline: Bool {
+        session.networkMonitor.isOnline && !isOfflineModeEnabled
+    }
+
     var body: some View {
         VStack(spacing: 0) {
             HStack {
@@ -22,20 +41,75 @@ struct SettingsSidebarList: View {
 
             Divider()
 
-            List(SettingsSection.allCases, selection: $selection) { section in
+            List(selection: $selection) {
-                Label(section.title, systemImage: section.icon)
+                ForEach(SettingsCategory.allCases) { category in
-                    .tag(section)
+                    let sections = SettingsSection.allCases.filter { $0.category == category }
+                    Section {
+                        ForEach(sections) { section in
+                            Label(section.title, systemImage: section.icon)
+                                .tag(section)
+                        }
+                    } header: {
+                        if let title = category.title {
+                            HStack(spacing: 6) {
+                                Text(title)
+                                // Not hardcoded to `.workspace` specifically —
+                                // stays correct on its own as sections get
+                                // built, only shows while every section in
+                                // the category is still `!isImplemented`.
+                                if sections.allSatisfy({ !$0.isImplemented }) {
+                                    Text("Coming Soon")
+                                        .font(.system(size: 9, weight: .semibold))
+                                        .foregroundStyle(.secondary)
+                                        .padding(.horizontal, 6)
+                                        .padding(.vertical, 2)
+                                        .background(.secondary.opacity(0.15), in: Capsule())
+                                }
+                            }
+                        }
+                    }
+                }
             }
             .listStyle(.sidebar)
 
             Divider()
 
+            versionFooter
+
+            Divider()
+
             Button("Done", action: onDone)
                 .keyboardShortcut(.cancelAction)
                 .buttonStyle(.borderedProminent)
                 .frame(maxWidth: .infinity)
                 .padding(12)
         }
+        // Keyed to connectivity, not a one-shot `.task {}` — reconnecting
+        // (or turning the manual Offline Mode toggle back off) re-fires
+        // this automatically instead of leaving the footer stuck on
+        // whatever it last knew, or blank, until Settings is reopened.
+        .task(id: isEffectivelyOnline) { await refreshOutlineVersion() }
+    }
+
+    private var versionFooter: some View {
+        VStack(alignment: .leading, spacing: 2) {
+            Text("Outpost \(OutpostVersion.displayString)")
+            if let outlineVersion {
+                Text("Outline \(outlineVersion)")
+            } else if !isEffectivelyOnline {
+                Text("Outline — offline")
+            }
+        }
+        .font(.caption2)
+        .foregroundStyle(.tertiary)
+        .frame(maxWidth: .infinity, alignment: .leading)
+        .padding(.horizontal, 16)
+        .padding(.vertical, 8)
+    }
+
+    private func refreshOutlineVersion() async {
+        guard isEffectivelyOnline, let apiClient = session.apiClient else { return }
+        outlineVersion = try? await apiClient.installationInfo().version
     }
 }
 #endif

Outpost/Features/Auth/AuthHeaderView.swift

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

Outpost/Features/Collections/ContentView_macOS.swift

@@ -40,25 +40,63 @@ struct ContentView_macOS: View {
     }
 
     var body: some View {
+        // A totally separate top-level branch, not content swapped inside
+        // one persistent `NavigationSplitView` — that was tried first (an
+        // `if/else` inside a single split view, then an explicit `.id()` on
+        // just the detail pane) and neither reliably replaced the detail
+        // pane's content on macOS: `NavigationSplitView` bridges to
+        // `NSSplitViewController`, and swapping a `NavigationStack` with
+        // real push history for a plain view inside one persisting instance
+        // doesn't propagate the way plain SwiftUI identity rules would
+        // suggest. A different `if` branch is a genuinely different view
+        // hierarchy, so there's no existing split view instance for AppKit
+        // to get confused about reusing.
+        if navigation.isShowingSettings {
+            settingsContent
+        } else {
+            mainContent
+        }
+    }
+
+    private var settingsContent: some View {
         NavigationSplitView {
-            Group {
+            SettingsSidebarList(
-                if navigation.isShowingSettings {
+                selection: selectedSettingsSectionBinding,
-                    SettingsSidebarList(
+                onDone: { navigation.isShowingSettings = false }
-                        selection: selectedSettingsSectionBinding,
+            )
-                        onDone: { navigation.isShowingSettings = false }
+            .navigationSplitViewColumnWidth(min: 220, ideal: 260)
-                    )
+        } detail: {
-                } else {
+            SettingsView(section: navigation.selectedSettingsSection ?? .appearance)
-                    VStack(spacing: 0) {
+        }
-                        SidebarSearchField(text: $globalSearchQuery)
+        .navigationTitle("")
-                        Divider()
+        .toolbar {
-                        if isOfflineModeEnabled || !session.networkMonitor.isOnline {
+            ToolbarItem(placement: .navigation) {
-                            OfflineBanner(isManual: isOfflineModeEnabled)
+                HStack(spacing: 6) {
-                            Divider()
+                    Image(systemName: "gearshape.fill")
-                        }
+                    Text("Settings")
-                        sidebar
-                        AccountFooter()
-                    }
                 }
+                .font(.headline)
+                .padding(.horizontal, 10)
+                .padding(.vertical, 4)
+                .background(.fill.tertiary, in: Capsule())
+            }
+        }
+    }
+
+    private var mainContent: some View {
+        NavigationSplitView {
+            VStack(spacing: 0) {
+                SidebarSearchField(text: $globalSearchQuery)
+                Divider()
+                if isOfflineModeEnabled {
+                    OfflineBanner(isManual: true)
+                    Divider()
+                } else if !session.networkMonitor.isOnline {
+                    OfflineConnectionPromptBanner(onEnableOfflineMode: { isOfflineModeEnabled = true })
+                    Divider()
+                }
+                sidebar
+                AccountFooter()
             }
             .navigationSplitViewColumnWidth(min: 220, ideal: 260)
         } detail: {
@@ -97,7 +135,7 @@ struct ContentView_macOS: View {
             // `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 !navigation.isShowingSettings && !(isShowingHome && documentPath.isEmpty) {
+            if !(isShowingHome && documentPath.isEmpty) {
                 ToolbarItem(placement: .primaryAction) {
                     contextualSearchField
                 }
@@ -167,12 +205,7 @@ struct ContentView_macOS: View {
     @ViewBuilder
     private var leadingToolbarContent: some View {
         Group {
-            if navigation.isShowingSettings {
+            if !trimmedGlobalQuery.isEmpty {
-                HStack(spacing: 6) {
-                    Image(systemName: "gearshape.fill")
-                    Text("Settings")
-                }
-            } else if !trimmedGlobalQuery.isEmpty {
                 HStack(spacing: 6) {
                     Image(systemName: "magnifyingglass")
                     Text("Search")
@@ -251,7 +284,6 @@ struct ContentView_macOS: View {
         globalSearchQuery = ""
         selectedCollection = collection
         isContextualSearchExpanded = true
-        navigation.isShowingSettings = false
         Task { @MainActor in
             isContextualSearchFocused = true
         }
@@ -262,13 +294,11 @@ struct ContentView_macOS: View {
     /// hierarchy immediately rather than just the leaf.
     private func selectDocumentChain(_ collection: OutlineCollection, _ chain: [OutlineDocument]) {
         selectedCollection = collection
-        navigation.isShowingSettings = false
         replaceDocumentPath(with: chain)
     }
 
     /// Flat-list / search-result clicks: no known ancestors, single-level push.
     private func openDocument(_ document: OutlineDocument) {
-        navigation.isShowingSettings = false
         replaceDocumentPath(with: [document])
     }
 
@@ -287,14 +317,7 @@ struct ContentView_macOS: View {
 
     @ViewBuilder
     private var detail: some View {
-        if navigation.isShowingSettings {
+        if let apiClient = session.apiClient {
-            // Deliberately not a `NavigationStack` destination or a separate
-            // window — it's swapped into the same detail pane Home/
-            // collections use, alongside the real sidebar (now showing
-            // `SettingsSidebarList` instead of the collections tree) rather
-            // than a page with its own nested mini sidebar.
-            SettingsView(section: navigation.selectedSettingsSection ?? .appearance)
-        } else if let apiClient = session.apiClient {
             // A fresh NavigationStack per collection (or when entering/leaving
             // search), so switching either also clears any pushed document.
             NavigationStack(path: $documentPath) {

Outpost/Features/Collections/DocumentReaderView.swift

@@ -12,6 +12,7 @@ import OutlineKit
 struct DocumentReaderView: View {
     @Environment(SessionStore.self) private var session
     @Environment(StarStore.self) private var starStore
+    @AppStorage(CachingOutlineAPIClient.offlineModeDefaultsKey) private var isOfflineModeEnabled = false
 
     @State private var viewModel: DocumentReaderViewModel
     let apiClient: OutlineAPIClient
@@ -56,6 +57,15 @@ struct DocumentReaderView: View {
         self.onDocumentCreated = onDocumentCreated
     }
 
+    /// New Document, editing, pin/star/subscribe, and Full Width all queue
+    /// and sync later (see `CachingOutlineAPIClient`) — everything else here
+    /// (sharing, permissions, move/archive/delete/duplicate/templatize,
+    /// history, insights, export) hits the server directly with no offline
+    /// path, so it's disabled rather than left to fail confusingly on tap.
+    private var isEffectivelyOnline: Bool {
+        session.networkMonitor.isOnline && !isOfflineModeEnabled
+    }
+
     var body: some View {
         ScrollView {
             VStack(alignment: .leading, spacing: 12) {
@@ -82,6 +92,7 @@ struct DocumentReaderView: View {
                     NativeTextViewWrapper(
                         text: $viewModel.text,
                         configuration: .init(heightBehavior: .fitsContent),
+                        documentId: viewModel.documentId,
                         isEditable: viewModel.isEditing
                     )
 
@@ -110,7 +121,8 @@ struct DocumentReaderView: View {
                 } label: {
                     Image(systemName: "square.and.arrow.up")
                 }
-                .help("Share")
+                .help(isEffectivelyOnline ? "Share" : "Sharing needs an internet connection")
+                .disabled(!isEffectivelyOnline)
                 .popover(isPresented: $isShowingShareSheet, arrowEdge: .bottom) {
                     DocumentShareSheet(apiClient: apiClient, documentId: viewModel.documentId)
                 }
@@ -235,7 +247,8 @@ struct DocumentReaderView: View {
             viewModel.isPinned,
             viewModel.isInsightsEnabled ?? false,
             viewModel.isFullWidth,
-            viewModel.isEditing
+            viewModel.isEditing,
+            isEffectivelyOnline
         ].map(String.init).joined(separator: "-")
     }
 
@@ -305,27 +318,33 @@ struct DocumentReaderView: View {
         Button("Permissions…") {
             isShowingShareSheet = true
         }
+        .disabled(!isEffectivelyOnline)
 
         Divider()
 
         Button("Templatize") {
             Task { await templatize() }
         }
+        .disabled(!isEffectivelyOnline)
         Button("Duplicate") {
             Task { await duplicate() }
         }
+        .disabled(!isEffectivelyOnline)
         Button("Unpublish") {
             isShowingUnpublishConfirmation = true
         }
+        .disabled(!isEffectivelyOnline)
         Button("Archive…") {
             isShowingArchiveConfirmation = true
         }
+        .disabled(!isEffectivelyOnline)
 
         Divider()
 
         Button("Move") {
             isShowingMoveSheet = true
         }
+        .disabled(!isEffectivelyOnline)
         // Multipart file upload is its own subsystem — deferred rather than
         // half-built here.
         Button("Import Document…") {}
@@ -342,9 +361,13 @@ struct DocumentReaderView: View {
         Button("History") {
             isShowingHistorySheet = true
         }
+        .disabled(!isEffectivelyOnline)
         Button("Insights") {
             isShowingInsightsSheet = true
         }
+        .disabled(!isEffectivelyOnline)
+        // Present/Search in Document both read `documents.info`, which is
+        // read-through cached — they work offline on whatever's cached.
         Button("Present") {
             isShowingPresentSheet = true
         }
@@ -354,6 +377,7 @@ struct DocumentReaderView: View {
         Button("Download") {
             Task { await download() }
         }
+        .disabled(!isEffectivelyOnline)
         Button("Copy") {
             Task { await copyMarkdown() }
         }
@@ -370,6 +394,7 @@ struct DocumentReaderView: View {
             get: { viewModel.isInsightsEnabled ?? false },
             set: { _ in Task { await toggleInsights() } }
         ))
+        .disabled(!isEffectivelyOnline)
         // 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
@@ -386,6 +411,7 @@ struct DocumentReaderView: View {
         Button("Delete…", role: .destructive) {
             isShowingDeleteConfirmation = true
         }
+        .disabled(!isEffectivelyOnline)
     }
 
     private func star() async {

Outpost/Features/Collections/OfflineConnectionPromptBanner.swift

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

Outpost/Features/Home/HomeViewModel.swift

@@ -57,25 +57,33 @@ final class HomeViewModel {
     /// 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.
+    /// transient network hiccup (or, offline, `listPins` failing outright —
+    /// it isn't one of the cached endpoints) shouldn't pop the refresh
+    /// banner. This needs the *throwing* pinned-fetch specifically: the
+    /// plain `fetchPinned()` used elsewhere collapses any failure to `[]`,
+    /// which used to read here as "pins changed" against whatever was
+    /// already displayed and falsely popped the banner on every offline
+    /// poll.
     func checkForRemoteChanges(tab: HomeTab) async {
-        async let freshPinned = fetchPinned()
+        async let freshPinnedTask = fetchPinnedThrowing()
         guard let freshTab = try? await fetch(tab: tab) else { return }
-        let pinned = await freshPinned
+        guard let pinned = try? await freshPinnedTask else { return }
         if Self.fingerprint(pinned) != Self.fingerprint(pinnedDocuments)
             || Self.fingerprint(freshTab) != Self.fingerprint(documents(for: tab)) {
             hasRemoteChanges = true
         }
     }
 
+    private func fetchPinned() async -> [OutlineDocument] {
+        (try? await fetchPinnedThrowing()) ?? []
+    }
+
     /// `pins.list` only returns pin records, not the documents themselves —
     /// fetches each pinned document individually. Pins are a small curated
     /// set (unlike a full collection tree), so the N+1 here is acceptable
     /// where it wouldn't be in the sidebar.
-    private func fetchPinned() async -> [OutlineDocument] {
+    private func fetchPinnedThrowing() async throws -> [OutlineDocument] {
-        guard let pins = try? await apiClient.listPins(ListPinsRequest(collectionId: nil)) else {
+        let pins = try await apiClient.listPins(ListPinsRequest(collectionId: nil))
-            return []
-        }
         var documents: [OutlineDocument] = []
         for pin in pins {
             if let document = try? await apiClient.documentInfo(id: pin.documentId) {

Outpost/Root/AppNavigation.swift

@@ -1,27 +1,124 @@
 import Observation
 
-enum SettingsSection: String, CaseIterable, Identifiable, Hashable {
+/// Top-level groupings shown as section headers in `SettingsSidebarList`.
-    case appearance, account, offlineSync, advanced, about
+/// `general` holds everything that's ours, not Outline's own settings
+/// categories — labeled "Outpost" so it reads as clearly distinct from the
+/// Outline-sourced groups below it.
+enum SettingsCategory: String, CaseIterable, Identifiable {
+    case general
+    case account
+    case workspace
 
     var id: String { rawValue }
 
+    var title: String? {
+        switch self {
+        case .general: return "Outpost"
+        case .account: return "Account"
+        case .workspace: return "Workspace"
+        }
+    }
+}
+
+/// One entry in the Settings sidebar. Mirrors Outline's own settings
+/// categories (Account/Workspace) so this app's settings read as a native
+/// counterpart to the web app's, plus a `general` group for things that are
+/// ours and don't map onto Outline's structure (offline/sync, advanced,
+/// about, appearance). Outline's own version info moved to the sidebar
+/// footer (`SettingsSidebarList`) instead of a standalone
+/// Integrations & Installation section.
+///
+/// Most of the Account/Workspace cases are navigation-only for now —
+/// `SettingsView` renders a "Coming Soon" placeholder for anything not
+/// explicitly built yet. Content lands section by section.
+enum SettingsSection: String, CaseIterable, Identifiable, Hashable {
+    // General (ours)
+    case appearance, offlineSync, advanced, about
+
+    // Account
+    case profile, preferences, notifications, passkeys, apiAccess
+
+    // Workspace
+    case details, authentication, security, ai, members, groups, templates, emojis, applications, shared, links, webhooks, importData, exportData
+
+    var id: String { rawValue }
+
+    var category: SettingsCategory {
+        switch self {
+        case .appearance, .offlineSync, .advanced, .about:
+            return .general
+        case .profile, .preferences, .notifications, .passkeys, .apiAccess:
+            return .account
+        case .details, .authentication, .security, .ai, .members, .groups, .templates, .emojis, .applications, .shared, .links, .webhooks, .importData, .exportData:
+            return .workspace
+        }
+    }
+
     var title: String {
         switch self {
         case .appearance: return "Appearance"
-        case .account: return "Account"
         case .offlineSync: return "Offline & Sync"
         case .advanced: return "Advanced"
         case .about: return "About"
+        case .profile: return "Profile"
+        case .preferences: return "Preferences"
+        case .notifications: return "Notifications"
+        case .passkeys: return "Passkeys"
+        case .apiAccess: return "API & Access"
+        case .details: return "Details"
+        case .authentication: return "Authentication"
+        case .security: return "Security"
+        case .ai: return "AI"
+        case .members: return "Members"
+        case .groups: return "Groups"
+        case .templates: return "Templates"
+        case .emojis: return "Emojis"
+        case .applications: return "Applications"
+        case .shared: return "Shared"
+        case .links: return "Links"
+        case .webhooks: return "Webhooks"
+        case .importData: return "Import"
+        case .exportData: return "Export"
         }
     }
 
     var icon: String {
         switch self {
         case .appearance: return "paintbrush"
-        case .account: return "person.crop.circle"
         case .offlineSync: return "arrow.triangle.2.circlepath"
         case .advanced: return "wrench.and.screwdriver"
         case .about: return "info.circle"
+        case .profile: return "person.crop.circle"
+        case .preferences: return "gearshape"
+        case .notifications: return "bell"
+        case .passkeys: return "key"
+        case .apiAccess: return "chevron.left.forwardslash.chevron.right"
+        case .details: return "building.2"
+        case .authentication: return "lock"
+        case .security: return "shield"
+        case .ai: return "sparkles"
+        case .members: return "person.2"
+        case .groups: return "person.3"
+        case .templates: return "doc.on.doc"
+        case .emojis: return "face.smiling"
+        case .applications: return "app.badge"
+        case .shared: return "square.and.arrow.up.on.square"
+        case .links: return "link"
+        case .webhooks: return "bolt.horizontal"
+        case .importData: return "square.and.arrow.down"
+        case .exportData: return "square.and.arrow.up"
+        }
+    }
+
+    /// Everything actually built so far — everything else in Account/
+    /// Workspace renders a "Coming Soon" placeholder until its content is
+    /// specified and built.
+    var isImplemented: Bool {
+        switch self {
+        case .appearance, .offlineSync, .advanced, .about, .profile, .preferences, .notifications, .passkeys, .apiAccess:
+            return true
+        default:
+            return false
         }
     }
 }

Outpost/Root/RootView.swift

@@ -6,6 +6,18 @@ struct RootView: View {
     @State private var welcomeName: String?
     @State private var starStore = StarStore()
     @AppStorage("outpost.fullLocalSyncEnabled") private var isFullLocalSyncEnabled = false
+    @AppStorage(CachingOutlineAPIClient.offlineModeDefaultsKey) private var isOfflineModeEnabled = false
+
+    /// Real connectivity is only half of "can talk to the server" — the
+    /// manual Offline Mode toggle is the other half. Syncing needs to
+    /// resume on either one clearing, not just a real reconnect: turning
+    /// the toggle off while the network had been up the whole time never
+    /// changes `networkMonitor.isOnline`, so keying the flush task off that
+    /// alone left pending operations stuck until the next real network
+    /// blip.
+    private var isEffectivelyOnline: Bool {
+        session.networkMonitor.isOnline && !isOfflineModeEnabled
+    }
 
     var body: some View {
         ZStack {
@@ -33,17 +45,31 @@ struct RootView: View {
                 starStore.reset()
             }
         }
-        // Replay whatever queued up while offline the moment the network's
+        // Replay whatever queued up while offline the moment either signal
-        // back — no need to wait for the user to open Settings and hit Retry.
+        // clears — a real reconnect, or the user turning Offline Mode back
-        // Also catches Full Local Sync back up immediately on reconnect,
+        // off — no need to wait for the user to open Settings and hit Retry.
-        // rather than leaving it to wait out the rest of the periodic loop
+        // Also catches Full Local Sync back up immediately, rather than
-        // below.
+        // leaving it to wait out the rest of the periodic loop below.
-        .task(id: session.networkMonitor.isOnline) {
+        //
-            guard session.networkMonitor.isOnline, let cachingClient = session.cachingClient else { return }
+        // The flush itself gets a retry loop with a cooloff, not just one
-            _ = await cachingClient.flushPendingOperations()
+        // attempt: a single transient failure (one bad operation, a blip
+        // mid-flush) used to leave everything else stuck until the user
+        // manually hit Retry or connectivity changed again. Keeps retrying
+        // every 5 minutes for as long as *anything* is still pending and
+        // this signal stays on — stops on its own once the queue is empty,
+        // and `.task(id:)` cancels/restarts it automatically if
+        // isEffectivelyOnline flips again in the meantime.
+        .task(id: isEffectivelyOnline) {
+            guard isEffectivelyOnline, let cachingClient = session.cachingClient else { return }
             if isFullLocalSyncEnabled {
                 _ = await cachingClient.performFullSync()
             }
+            while !Task.isCancelled {
+                _ = await cachingClient.flushPendingOperations()
+                let remaining = await cachingClient.pendingOperations()
+                guard !remaining.isEmpty else { break }
+                try? await Task.sleep(for: .seconds(300))
+            }
         }
         // Fully automatic — this is the only place Full Local Sync actually
         // runs from (Settings' "Sync Now" is just an on-demand nudge at the
@@ -55,7 +81,7 @@ struct RootView: View {
         .task(id: isFullLocalSyncEnabled) {
             guard isFullLocalSyncEnabled else { return }
             while !Task.isCancelled {
-                if session.networkMonitor.isOnline, let cachingClient = session.cachingClient {
+                if isEffectivelyOnline, let cachingClient = session.cachingClient {
                     _ = await cachingClient.performFullSync()
                 }
                 try? await Task.sleep(for: .seconds(1200))

Outpost/Root/SessionStore.swift

@@ -11,9 +11,13 @@ final class SessionStore {
     private let defaults: UserDefaults
 
     var isSignedIn: Bool
+    private(set) var userId: String?
     var userName: String?
     var userEmail: String?
     var userAvatarURL: URL?
+    var userLanguage: String?
+    var userPreferences: OutlineUserPreferences?
+    var userNotificationSettings: [String: Bool]?
     var teamName: String?
     var teamAvatarURL: URL?
     private(set) var apiClient: OutlineAPIClient?
@@ -35,11 +39,27 @@ final class SessionStore {
     init(tokenStore: TokenStoring = KeychainTokenStore(), defaults: UserDefaults = .standard) {
         self.tokenStore = tokenStore
         self.defaults = defaults
-        self.isSignedIn = (try? tokenStore.token()) != nil
         self.cacheStore = (try? OfflineCacheStore.makeContainer()).map(OfflineCacheStore.init(modelContainer:))
 
-        if isSignedIn, let serverURL {
+        let hasToken = (try? tokenStore.token()) != nil
-            (apiClient, cachingClient) = Self.makeAPIClient(serverURL: serverURL, tokenStore: tokenStore, cache: cacheStore)
+        let storedServerURL = defaults.string(forKey: Self.serverURLDefaultsKey).flatMap(URL.init(string:))
+
+        if hasToken, let storedServerURL {
+            isSignedIn = true
+            (apiClient, cachingClient) = Self.makeAPIClient(serverURL: storedServerURL, tokenStore: tokenStore, cache: cacheStore)
+        } else {
+            // Keychain and the sandboxed UserDefaults container don't
+            // always survive together — a Keychain item written by an
+            // older-signed build can outlive a reinstall that wipes the
+            // container (or vice versa), leaving a token with no server or
+            // a server with no token. Clear whichever half survived rather
+            // than showing a broken "signed in" UI with no working
+            // apiClient — a fresh sign-in rewrites both consistently.
+            if hasToken {
+                try? tokenStore.clear()
+            }
+            defaults.removeObject(forKey: Self.serverURLDefaultsKey)
+            isSignedIn = false
         }
     }
 
@@ -68,9 +88,13 @@ final class SessionStore {
         try? tokenStore.clear()
         defaults.removeObject(forKey: Self.serverURLDefaultsKey)
         isSignedIn = false
+        userId = nil
         userName = nil
         userEmail = nil
         userAvatarURL = nil
+        userLanguage = nil
+        userPreferences = nil
+        userNotificationSettings = nil
         teamName = nil
         teamAvatarURL = nil
         apiClient = nil
@@ -85,13 +109,30 @@ final class SessionStore {
         apply(user: auth.user, team: auth.team, serverURL: serverURL)
     }
 
+    /// Settings calls this after a successful name/avatar change so the
+    /// sidebar's account footer and everywhere else reading these reflect
+    /// it immediately, without waiting for the next `auth.info` refresh.
+    func applyUpdatedProfile(_ user: OutlineUser) {
+        guard let serverURL else { return }
+        userId = user.id
+        userName = user.name
+        userAvatarURL = user.avatarUrl.flatMap { URL(string: $0, relativeTo: serverURL)?.absoluteURL }
+        userLanguage = user.language
+        userPreferences = user.preferences
+        userNotificationSettings = user.notificationSettings
+    }
+
     private func apply(user: OutlineUser, team: OutlineTeam, serverURL: URL) {
+        userId = user.id
         userName = user.name
         userEmail = user.email
         // Outline can return either an absolute URL or a server-relative path
         // (e.g. `/api/files.get?key=...`) for avatarUrl — resolve against the
         // configured server so relative paths don't fail as "unsupported URL".
         userAvatarURL = user.avatarUrl.flatMap { URL(string: $0, relativeTo: serverURL)?.absoluteURL }
+        userLanguage = user.language
+        userPreferences = user.preferences
+        userNotificationSettings = user.notificationSettings
         teamName = team.name
         teamAvatarURL = team.avatarUrl.flatMap { URL(string: $0, relativeTo: serverURL)?.absoluteURL }
     }

Outpost/Support/AvatarBadge.swift

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

Outpost/Support/NSImage+JPEGData.swift

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

Outpost/Support/OutlineLocale.swift

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

Outpost/Support/OutpostVersion.swift

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