diff --git a/.gitmodules b/.gitmodules
new file mode 100644
index 0000000..8c99c45
--- /dev/null
+++ b/.gitmodules
@@ -0,0 +1,3 @@
+[submodule "docs/reference/outline-openapi"]
+	path = docs/reference/outline-openapi
+	url = https://github.com/outline/openapi.git
diff --git a/OutlineKit/.gitignore b/OutlineKit/.gitignore
new file mode 100644
index 0000000..29a1e94
--- /dev/null
+++ b/OutlineKit/.gitignore
@@ -0,0 +1,3 @@
+.build/
+.swiftpm/
+.DS_Store
diff --git a/OutlineKit/Package.swift b/OutlineKit/Package.swift
new file mode 100644
index 0000000..8a929b8
--- /dev/null
+++ b/OutlineKit/Package.swift
@@ -0,0 +1,22 @@
+// swift-tools-version:5.9
+import PackageDescription
+
+let package = Package(
+    name: "OutlineKit",
+    platforms: [
+        .iOS(.v17),
+        .macOS(.v14)
+    ],
+    products: [
+        .library(name: "OutlineKit", targets: ["OutlineKit"])
+    ],
+    targets: [
+        .target(
+            name: "OutlineKit"
+        ),
+        .testTarget(
+            name: "OutlineKitTests",
+            dependencies: ["OutlineKit"]
+        )
+    ]
+)
diff --git a/OutlineKit/Sources/OutlineKit/Auth/KeychainTokenStore.swift b/OutlineKit/Sources/OutlineKit/Auth/KeychainTokenStore.swift
new file mode 100644
index 0000000..83c283f
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Auth/KeychainTokenStore.swift
@@ -0,0 +1,56 @@
+import Foundation
+import Security
+
+public final class KeychainTokenStore: TokenStoring, @unchecked Sendable {
+    private let service: String
+    private let account: String
+
+    public init(service: String = "com.outpost.outlinekit", account: String = "outline-api-token") {
+        self.service = service
+        self.account = account
+    }
+
+    public func token() throws -> String {
+        var query = baseQuery()
+        query[kSecReturnData as String] = true
+        query[kSecMatchLimit as String] = kSecMatchLimitOne
+
+        var result: AnyObject?
+        let status = SecItemCopyMatching(query as CFDictionary, &result)
+        guard status == errSecSuccess, let data = result as? Data, let token = String(data: data, encoding: .utf8) else {
+            throw TokenStoreError.notFound
+        }
+        return token
+    }
+
+    public func store(_ token: String) throws {
+        let data = Data(token.utf8)
+        let query = baseQuery()
+
+        let existsStatus = SecItemCopyMatching(query as CFDictionary, nil)
+        if existsStatus == errSecSuccess {
+            let updateStatus = SecItemUpdate(query as CFDictionary, [kSecValueData as String: data] as CFDictionary)
+            guard updateStatus == errSecSuccess else { throw TokenStoreError.storeFailed(updateStatus) }
+        } else {
+            var addQuery = query
+            addQuery[kSecValueData as String] = data
+            let addStatus = SecItemAdd(addQuery as CFDictionary, nil)
+            guard addStatus == errSecSuccess else { throw TokenStoreError.storeFailed(addStatus) }
+        }
+    }
+
+    public func clear() throws {
+        let status = SecItemDelete(baseQuery() as CFDictionary)
+        guard status == errSecSuccess || status == errSecItemNotFound else {
+            throw TokenStoreError.deleteFailed(status)
+        }
+    }
+
+    private func baseQuery() -> [String: Any] {
+        [
+            kSecClass as String: kSecClassGenericPassword,
+            kSecAttrService as String: service,
+            kSecAttrAccount as String: account
+        ]
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Auth/TokenStoring.swift b/OutlineKit/Sources/OutlineKit/Auth/TokenStoring.swift
new file mode 100644
index 0000000..90a6c1e
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Auth/TokenStoring.swift
@@ -0,0 +1,14 @@
+import Foundation
+
+/// Boundary over wherever the API bearer token lives. Tokens never touch UserDefaults or logs.
+public protocol TokenStoring: Sendable {
+    func token() throws -> String
+    func store(_ token: String) throws
+    func clear() throws
+}
+
+public enum TokenStoreError: Error, Sendable {
+    case notFound
+    case storeFailed(OSStatus)
+    case deleteFailed(OSStatus)
+}
diff --git a/OutlineKit/Sources/OutlineKit/Collaboration/HocuspocusConnection.swift b/OutlineKit/Sources/OutlineKit/Collaboration/HocuspocusConnection.swift
new file mode 100644
index 0000000..962b24b
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Collaboration/HocuspocusConnection.swift
@@ -0,0 +1,103 @@
+import Foundation
+
+/// Connection lifecycle for Outline's Hocuspocus collaboration socket
+/// (`wss://<host>/collaboration/document.<id>`) — see `docs/ARCHITECTURE.md`
+/// section 2. This is transport only: it opens the socket, authenticates,
+/// and hands raw binary frames to a handler. It does **not** speak the Yjs
+/// sync/awareness wire protocol or touch a `Y.Doc` — that needs the YSwift
+/// package (not yet added to this project; add it via Xcode's Package
+/// Dependencies, pointed at `https://github.com/y-crdt/yswift`, and confirm
+/// it resolves/builds before writing anything on top of this) plus the
+/// ProseMirror⇄markdown schema mapping described in ARCHITECTURE.md
+/// section 4, neither of which exist yet. Do not treat this class as "collab
+/// is working" — it's the socket handshake only.
+public actor HocuspocusConnection {
+    public enum State: Equatable, Sendable {
+        case disconnected
+        case connecting
+        case connected
+        case failed(String)
+    }
+
+    public private(set) var state: State = .disconnected
+
+    private let documentId: String
+    private let baseURL: URL
+    private let tokenStore: TokenStoring
+    private var task: URLSessionWebSocketTask?
+    private var receiveLoopTask: Task<Void, Never>?
+    private var onFrame: (@Sendable (Data) -> Void)?
+
+    public init(documentId: String, baseURL: URL, tokenStore: TokenStoring) {
+        self.documentId = documentId
+        self.baseURL = baseURL
+        self.tokenStore = tokenStore
+    }
+
+    /// `onFrame` is called for every binary frame received, on an arbitrary
+    /// executor — callers that touch UI state must hop back to `@MainActor`
+    /// themselves.
+    public func connect(onFrame: @escaping @Sendable (Data) -> Void) {
+        guard state != .connected, state != .connecting else { return }
+        self.onFrame = onFrame
+
+        guard let token = try? tokenStore.token(), let wsURL = webSocketURL() else {
+            state = .failed("Missing token or invalid server URL.")
+            return
+        }
+
+        state = .connecting
+        var request = URLRequest(url: wsURL)
+        request.setValue("Bearer \(token)", forHTTPHeaderField: "Authorization")
+
+        let session = URLSession(configuration: .default)
+        let webSocketTask = session.webSocketTask(with: request)
+        task = webSocketTask
+        webSocketTask.resume()
+        state = .connected
+
+        receiveLoopTask = Task { [weak self] in
+            await self?.receiveLoop()
+        }
+    }
+
+    public func disconnect() {
+        receiveLoopTask?.cancel()
+        receiveLoopTask = nil
+        task?.cancel(with: .goingAway, reason: nil)
+        task = nil
+        state = .disconnected
+    }
+
+    public func send(_ data: Data) async throws {
+        guard let task else { return }
+        try await task.send(.data(data))
+    }
+
+    private func receiveLoop() async {
+        guard let task else { return }
+        while !Task.isCancelled {
+            do {
+                let message = try await task.receive()
+                switch message {
+                case .data(let data):
+                    onFrame?(data)
+                case .string(let text):
+                    onFrame?(Data(text.utf8))
+                @unknown default:
+                    break
+                }
+            } catch {
+                state = .failed(error.localizedDescription)
+                return
+            }
+        }
+    }
+
+    private func webSocketURL() -> URL? {
+        guard var components = URLComponents(url: baseURL, resolvingAgainstBaseURL: false) else { return nil }
+        components.scheme = components.scheme == "http" ? "ws" : "wss"
+        components.path = "/collaboration/document.\(documentId)"
+        return components.url
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Core/OutlineAPIClient.swift b/OutlineKit/Sources/OutlineKit/Core/OutlineAPIClient.swift
new file mode 100644
index 0000000..3604545
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Core/OutlineAPIClient.swift
@@ -0,0 +1,58 @@
+import Foundation
+
+/// REST-layer boundary. The CRDT/sync layer and editor UI layer depend only on this
+/// protocol, never on `LiveOutlineAPIClient`, so the transport can be swapped or mocked
+/// without touching callers.
+public protocol OutlineAPIClient: Sendable {
+    /// Validates the current token and identifies the signed-in user/workspace. Backed by `auth.info`.
+    func authInfo() async throws -> OutlineAuthInfo
+
+    func documentInfo(id: String) async throws -> OutlineDocument
+    func listDocuments(collectionId: String?, parentDocumentId: String?, offset: Int, limit: Int) async throws -> [OutlineDocument]
+    /// Full-text search with snippets/ranking. Backed by `documents.search`.
+    func searchDocuments(_ request: DocumentSearchRequest) async throws -> [OutlineDocumentSearchResult]
+    /// Title-only search — faster, no snippets. Backed by `documents.search_titles`.
+    func searchDocumentTitles(_ request: DocumentSearchTitlesRequest) async throws -> [OutlineDocument]
+    func createDocument(_ request: CreateDocumentRequest) async throws -> OutlineDocument
+    func updateDocument(_ request: UpdateDocumentRequest) async throws -> OutlineDocument
+    func starDocument(_ request: StarDocumentRequest) async throws -> OutlineStar
+    func templatizeDocument(_ request: TemplatizeDocumentRequest) async throws -> OutlineTemplate
+    func duplicateDocument(_ request: DuplicateDocumentRequest) async throws -> [OutlineDocument]
+    func unpublishDocument(_ request: UnpublishDocumentRequest) async throws -> OutlineDocument
+    func archiveDocument(id: String) async throws -> OutlineDocument
+    func moveDocument(_ request: MoveDocumentRequest) async throws
+    func deleteDocument(_ request: DeleteDocumentRequest) async throws
+    /// Requires insights to be enabled on the document server-side. Backed by `documents.insights`.
+    func documentInsights(_ request: DocumentInsightsRequest) async throws -> [OutlineDocumentInsight]
+    /// Backed by `revisions.list` — omits full body content for performance.
+    func listRevisions(_ request: ListRevisionsRequest) async throws -> [OutlineRevision]
+    /// Returns the document's markdown source directly (not a file operation job). Backed by `documents.export`.
+    func exportDocument(id: String) async throws -> String
+    func createShare(_ request: CreateShareRequest) async throws -> OutlineShare
+    func shareInfo(documentId: String) async throws -> OutlineShare?
+    func updateShare(_ request: UpdateShareRequest) async throws -> OutlineShare
+    /// See `OutlinePin` — best-effort, not in the vendored spec.
+    func createPin(_ request: CreatePinRequest) async throws -> OutlinePin
+    func listPins(_ request: ListPinsRequest) async throws -> [OutlinePin]
+    func deletePin(id: String) async throws
+    /// See `OutlineSubscription` — best-effort, not in the vendored spec.
+    func createSubscription(_ request: CreateSubscriptionRequest) async throws -> OutlineSubscription
+    func listSubscriptions(_ request: ListSubscriptionsRequest) async throws -> [OutlineSubscription]
+    func deleteSubscription(id: String) async throws
+    /// Historical view records, not live presence. Backed by `views.list`.
+    func listViews(_ request: ListViewsRequest) async throws -> [OutlineView]
+
+    func listCollections(offset: Int, limit: Int) async throws -> [OutlineCollection]
+    func collectionInfo(id: String) async throws -> OutlineCollection
+    func updateCollection(_ request: UpdateCollectionRequest) async throws -> OutlineCollection
+    func deleteCollection(id: String) async throws
+    /// Kicks off an async export job — this only wraps the trigger, not polling
+    /// for completion or downloading the resulting file.
+    func exportCollection(_ request: ExportCollectionRequest) async throws -> OutlineFileOperation
+    func starCollection(_ request: StarCollectionRequest) async throws -> OutlineStar
+    /// Every star across both documents and collections for the current user. Backed by `stars.list`.
+    func listStars(_ request: ListStarsRequest) async throws -> [OutlineStar]
+    func deleteStar(id: String) async throws
+
+    func currentUser() async throws -> OutlineUser
+}
diff --git a/OutlineKit/Sources/OutlineKit/Core/OutlineAPIError.swift b/OutlineKit/Sources/OutlineKit/Core/OutlineAPIError.swift
new file mode 100644
index 0000000..be4a50a
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Core/OutlineAPIError.swift
@@ -0,0 +1,10 @@
+import Foundation
+
+public enum OutlineAPIError: Error, Sendable {
+    case unauthorized
+    case notFound
+    case server(status: Int, message: String?)
+    case decoding(Error)
+    case transport(Error)
+    case tokenUnavailable
+}
diff --git a/OutlineKit/Sources/OutlineKit/Core/OutlineConfiguration.swift b/OutlineKit/Sources/OutlineKit/Core/OutlineConfiguration.swift
new file mode 100644
index 0000000..8bdc965
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Core/OutlineConfiguration.swift
@@ -0,0 +1,10 @@
+import Foundation
+
+/// Points at one self-hosted Outline instance's API root, e.g. `https://outline.example.com`.
+public struct OutlineConfiguration: Sendable {
+    public let baseURL: URL
+
+    public init(baseURL: URL) {
+        self.baseURL = baseURL
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/LiveOutlineAPIClient.swift b/OutlineKit/Sources/OutlineKit/LiveOutlineAPIClient.swift
new file mode 100644
index 0000000..19a3725
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/LiveOutlineAPIClient.swift
@@ -0,0 +1,326 @@
+import Foundation
+
+/// Talks to Outline's RPC-style REST API (`POST /api/<namespace>.<method>`, Bearer auth).
+public actor LiveOutlineAPIClient: OutlineAPIClient {
+    private let baseURL: URL
+    private let httpClient: HTTPClient
+    private let tokenStore: TokenStoring
+    private let decoder: JSONDecoder
+    private let encoder: JSONEncoder
+
+    public init(
+        configuration: OutlineConfiguration,
+        tokenStore: TokenStoring,
+        httpClient: HTTPClient = URLSessionHTTPClient()
+    ) {
+        self.baseURL = configuration.baseURL
+        self.tokenStore = tokenStore
+        self.httpClient = httpClient
+
+        let decoder = JSONDecoder()
+        decoder.dateDecodingStrategy = .iso8601
+        self.decoder = decoder
+
+        let encoder = JSONEncoder()
+        encoder.dateEncodingStrategy = .iso8601
+        self.encoder = encoder
+    }
+
+    public func authInfo() async throws -> OutlineAuthInfo {
+        try await post("auth.info", body: EmptyParams())
+    }
+
+    public func documentInfo(id: String) async throws -> OutlineDocument {
+        try await post("documents.info", body: DocumentInfoParams(id: id))
+    }
+
+    public func listDocuments(
+        collectionId: String?,
+        parentDocumentId: String?,
+        offset: Int,
+        limit: Int
+    ) async throws -> [OutlineDocument] {
+        try await post(
+            "documents.list",
+            body: DocumentListParams(
+                collectionId: collectionId,
+                parentDocumentId: parentDocumentId,
+                offset: offset,
+                limit: limit
+            )
+        )
+    }
+
+    public func searchDocuments(_ request: DocumentSearchRequest) async throws -> [OutlineDocumentSearchResult] {
+        try await post("documents.search", body: request)
+    }
+
+    public func searchDocumentTitles(_ request: DocumentSearchTitlesRequest) async throws -> [OutlineDocument] {
+        try await post("documents.search_titles", body: request)
+    }
+
+    public func createDocument(_ request: CreateDocumentRequest) async throws -> OutlineDocument {
+        try await post("documents.create", body: request)
+    }
+
+    public func updateDocument(_ request: UpdateDocumentRequest) async throws -> OutlineDocument {
+        try await post("documents.update", body: request)
+    }
+
+    public func starDocument(_ request: StarDocumentRequest) async throws -> OutlineStar {
+        try await post("stars.create", body: request)
+    }
+
+    public func templatizeDocument(_ request: TemplatizeDocumentRequest) async throws -> OutlineTemplate {
+        try await post("documents.templatize", body: request)
+    }
+
+    public func duplicateDocument(_ request: DuplicateDocumentRequest) async throws -> [OutlineDocument] {
+        let result: DuplicateDocumentResponse = try await post("documents.duplicate", body: request)
+        return result.documents
+    }
+
+    public func unpublishDocument(_ request: UnpublishDocumentRequest) async throws -> OutlineDocument {
+        try await post("documents.unpublish", body: request)
+    }
+
+    public func archiveDocument(id: String) async throws -> OutlineDocument {
+        try await post("documents.archive", body: DocumentIDRequest(id: id))
+    }
+
+    public func moveDocument(_ request: MoveDocumentRequest) async throws {
+        let _: MoveDocumentResponse = try await post("documents.move", body: request)
+    }
+
+    public func deleteDocument(_ request: DeleteDocumentRequest) async throws {
+        try await postForSuccess("documents.delete", body: request)
+    }
+
+    public func documentInsights(_ request: DocumentInsightsRequest) async throws -> [OutlineDocumentInsight] {
+        try await post("documents.insights", body: request)
+    }
+
+    public func listRevisions(_ request: ListRevisionsRequest) async throws -> [OutlineRevision] {
+        try await post("revisions.list", body: request)
+    }
+
+    public func exportDocument(id: String) async throws -> String {
+        try await post("documents.export", body: DocumentIDRequest(id: id))
+    }
+
+    public func createShare(_ request: CreateShareRequest) async throws -> OutlineShare {
+        try await post("shares.create", body: request)
+    }
+
+    public func shareInfo(documentId: String) async throws -> OutlineShare? {
+        do {
+            return try await post("shares.info", body: ShareInfoRequest(documentId: documentId))
+        } catch OutlineAPIError.notFound {
+            return nil
+        }
+    }
+
+    public func updateShare(_ request: UpdateShareRequest) async throws -> OutlineShare {
+        try await post("shares.update", body: request)
+    }
+
+    public func createPin(_ request: CreatePinRequest) async throws -> OutlinePin {
+        try await post("pins.create", body: request)
+    }
+
+    public func listPins(_ request: ListPinsRequest) async throws -> [OutlinePin] {
+        try await post("pins.list", body: request)
+    }
+
+    public func deletePin(id: String) async throws {
+        try await postForSuccess("pins.delete", body: StarIDParams(id: id))
+    }
+
+    public func createSubscription(_ request: CreateSubscriptionRequest) async throws -> OutlineSubscription {
+        try await post("subscriptions.create", body: request)
+    }
+
+    public func listSubscriptions(_ request: ListSubscriptionsRequest) async throws -> [OutlineSubscription] {
+        try await post("subscriptions.list", body: request)
+    }
+
+    public func deleteSubscription(id: String) async throws {
+        try await postForSuccess("subscriptions.delete", body: StarIDParams(id: id))
+    }
+
+    public func listViews(_ request: ListViewsRequest) async throws -> [OutlineView] {
+        try await post("views.list", body: request)
+    }
+
+    public func listCollections(offset: Int, limit: Int) async throws -> [OutlineCollection] {
+        try await post("collections.list", body: CollectionListParams(offset: offset, limit: limit))
+    }
+
+    public func collectionInfo(id: String) async throws -> OutlineCollection {
+        try await post("collections.info", body: CollectionInfoParams(id: id))
+    }
+
+    public func updateCollection(_ request: UpdateCollectionRequest) async throws -> OutlineCollection {
+        try await post("collections.update", body: request)
+    }
+
+    public func deleteCollection(id: String) async throws {
+        try await postForSuccess("collections.delete", body: CollectionInfoParams(id: id))
+    }
+
+    public func exportCollection(_ request: ExportCollectionRequest) async throws -> OutlineFileOperation {
+        let result: ExportCollectionResponse = try await post("collections.export", body: request)
+        return result.fileOperation
+    }
+
+    public func starCollection(_ request: StarCollectionRequest) async throws -> OutlineStar {
+        try await post("stars.create", body: request)
+    }
+
+    public func listStars(_ request: ListStarsRequest) async throws -> [OutlineStar] {
+        let result: ListStarsResponse = try await post("stars.list", body: request)
+        return result.stars
+    }
+
+    public func deleteStar(id: String) async throws {
+        try await postForSuccess("stars.delete", body: StarIDParams(id: id))
+    }
+
+    public func currentUser() async throws -> OutlineUser {
+        try await post("users.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
+        }
+
+        var request = URLRequest(url: baseURL.appendingPathComponent("api/\(path)"))
+        request.httpMethod = "POST"
+        request.setValue("application/json", forHTTPHeaderField: "Content-Type")
+        request.setValue("Bearer \(token)", forHTTPHeaderField: "Authorization")
+        request.httpBody = try encoder.encode(body)
+
+        let data: Data
+        let response: HTTPURLResponse
+        do {
+            (data, response) = try await httpClient.send(request)
+        } catch let error as OutlineAPIError {
+            throw error
+        } catch {
+            throw OutlineAPIError.transport(error)
+        }
+
+        guard (200...299).contains(response.statusCode) else {
+            let errorEnvelope = try? decoder.decode(OutlineErrorEnvelope.self, from: data)
+            switch response.statusCode {
+            case 401:
+                throw OutlineAPIError.unauthorized
+            case 404:
+                throw OutlineAPIError.notFound
+            default:
+                throw OutlineAPIError.server(status: response.statusCode, message: errorEnvelope?.message ?? errorEnvelope?.error)
+            }
+        }
+
+        do {
+            return try decoder.decode(OutlineEnvelope<Response>.self, from: data).data
+        } catch {
+            throw OutlineAPIError.decoding(error)
+        }
+    }
+
+    /// For endpoints shaped `{ "success": true }` instead of `{ "data": ... }`
+    /// (e.g. `collections.delete`) — `post(_:body:)`'s envelope decode doesn't fit.
+    private func postForSuccess<Body: Encodable>(_ path: String, body: Body) async throws {
+        guard let token = try? tokenStore.token() else {
+            throw OutlineAPIError.tokenUnavailable
+        }
+
+        var request = URLRequest(url: baseURL.appendingPathComponent("api/\(path)"))
+        request.httpMethod = "POST"
+        request.setValue("application/json", forHTTPHeaderField: "Content-Type")
+        request.setValue("Bearer \(token)", forHTTPHeaderField: "Authorization")
+        request.httpBody = try encoder.encode(body)
+
+        let data: Data
+        let response: HTTPURLResponse
+        do {
+            (data, response) = try await httpClient.send(request)
+        } catch let error as OutlineAPIError {
+            throw error
+        } catch {
+            throw OutlineAPIError.transport(error)
+        }
+
+        guard (200...299).contains(response.statusCode) else {
+            let errorEnvelope = try? decoder.decode(OutlineErrorEnvelope.self, from: data)
+            switch response.statusCode {
+            case 401:
+                throw OutlineAPIError.unauthorized
+            case 404:
+                throw OutlineAPIError.notFound
+            default:
+                throw OutlineAPIError.server(status: response.statusCode, message: errorEnvelope?.message ?? errorEnvelope?.error)
+            }
+        }
+
+        do {
+            let envelope = try decoder.decode(SuccessEnvelope.self, from: data)
+            guard envelope.success else {
+                throw OutlineAPIError.server(status: response.statusCode, message: nil)
+            }
+        } catch let error as OutlineAPIError {
+            throw error
+        } catch {
+            throw OutlineAPIError.decoding(error)
+        }
+    }
+}
+
+private struct ExportCollectionResponse: Decodable {
+    let fileOperation: OutlineFileOperation
+}
+
+private struct DuplicateDocumentResponse: Decodable {
+    let documents: [OutlineDocument]
+}
+
+private struct ListStarsResponse: Decodable {
+    let stars: [OutlineStar]
+}
+
+private struct StarIDParams: Encodable {
+    let id: String
+}
+
+private struct MoveDocumentResponse: Decodable {
+    let documents: [OutlineDocument]?
+    let collections: [OutlineCollection]?
+}
+
+private struct SuccessEnvelope: Decodable {
+    let success: Bool
+}
+
+private struct DocumentInfoParams: Encodable {
+    let id: String
+}
+
+private struct DocumentListParams: Encodable {
+    let collectionId: String?
+    let parentDocumentId: String?
+    let offset: Int
+    let limit: Int
+}
+
+private struct CollectionListParams: Encodable {
+    let offset: Int
+    let limit: Int
+}
+
+private struct CollectionInfoParams: Encodable {
+    let id: String
+}
+
+private struct EmptyParams: Encodable {}
diff --git a/OutlineKit/Sources/OutlineKit/Models/DocumentSearchTypes.swift b/OutlineKit/Sources/OutlineKit/Models/DocumentSearchTypes.swift
new file mode 100644
index 0000000..203ca6d
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Models/DocumentSearchTypes.swift
@@ -0,0 +1,36 @@
+import Foundation
+
+public enum DocumentSearchDateFilter: String, Codable, Sendable, CaseIterable {
+    case day
+    case week
+    case month
+    case year
+}
+
+public enum DocumentSearchSort: String, Codable, Sendable, CaseIterable {
+    case relevance
+    case createdAt
+    case updatedAt
+    case title
+}
+
+public enum DocumentSearchDirection: String, Codable, Sendable, CaseIterable {
+    case ascending = "ASC"
+    case descending = "DESC"
+}
+
+public enum DocumentStatusFilter: String, Codable, Sendable, CaseIterable {
+    case draft
+    case archived
+    case published
+}
+
+/// One hit from `documents.search` — includes the matched snippet and ranking
+/// that `documents.search_titles` doesn't provide.
+public struct OutlineDocumentSearchResult: Decodable, Sendable, Identifiable {
+    public let context: String
+    public let ranking: Double
+    public let document: OutlineDocument
+
+    public var id: String { document.id }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Models/OutlineAuthInfo.swift b/OutlineKit/Sources/OutlineKit/Models/OutlineAuthInfo.swift
new file mode 100644
index 0000000..7ee726b
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Models/OutlineAuthInfo.swift
@@ -0,0 +1,12 @@
+import Foundation
+
+/// Result of `auth.info` — confirms a token is valid and identifies the signed-in user/workspace.
+public struct OutlineAuthInfo: Codable, Sendable {
+    public let user: OutlineUser
+    public let team: OutlineTeam
+
+    public init(user: OutlineUser, team: OutlineTeam) {
+        self.user = user
+        self.team = team
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Models/OutlineCollection.swift b/OutlineKit/Sources/OutlineKit/Models/OutlineCollection.swift
new file mode 100644
index 0000000..e842e1a
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Models/OutlineCollection.swift
@@ -0,0 +1,29 @@
+import Foundation
+
+public struct OutlineCollection: Codable, Identifiable, Hashable, Sendable {
+    public let id: String
+    public let name: String
+    public let description: String?
+    public let color: String?
+    public let icon: String?
+    public let createdAt: Date
+    public let updatedAt: Date
+
+    public init(
+        id: String,
+        name: String,
+        description: String? = nil,
+        color: String? = nil,
+        icon: String? = nil,
+        createdAt: Date,
+        updatedAt: Date
+    ) {
+        self.id = id
+        self.name = name
+        self.description = description
+        self.color = color
+        self.icon = icon
+        self.createdAt = createdAt
+        self.updatedAt = updatedAt
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Models/OutlineDocument.swift b/OutlineKit/Sources/OutlineKit/Models/OutlineDocument.swift
new file mode 100644
index 0000000..8b44c6f
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Models/OutlineDocument.swift
@@ -0,0 +1,50 @@
+import Foundation
+
+public struct OutlineDocument: Codable, Identifiable, Hashable, Sendable {
+    public let id: String
+    public let title: String
+    public let text: String
+    public let emoji: String?
+    public let collectionId: String?
+    public let parentDocumentId: String?
+    public let url: String
+    public let revision: Int?
+    public let fullWidth: Bool?
+    public let createdAt: Date
+    public let updatedAt: Date
+    public let publishedAt: Date?
+    public let archivedAt: Date?
+    public let deletedAt: Date?
+
+    public init(
+        id: String,
+        title: String,
+        text: String,
+        emoji: String? = nil,
+        collectionId: String? = nil,
+        parentDocumentId: String? = nil,
+        url: String,
+        revision: Int? = nil,
+        fullWidth: Bool? = nil,
+        createdAt: Date,
+        updatedAt: Date,
+        publishedAt: Date? = nil,
+        archivedAt: Date? = nil,
+        deletedAt: Date? = nil
+    ) {
+        self.id = id
+        self.title = title
+        self.text = text
+        self.emoji = emoji
+        self.collectionId = collectionId
+        self.parentDocumentId = parentDocumentId
+        self.url = url
+        self.revision = revision
+        self.fullWidth = fullWidth
+        self.createdAt = createdAt
+        self.updatedAt = updatedAt
+        self.publishedAt = publishedAt
+        self.archivedAt = archivedAt
+        self.deletedAt = deletedAt
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Models/OutlineDocumentInsight.swift b/OutlineKit/Sources/OutlineKit/Models/OutlineDocumentInsight.swift
new file mode 100644
index 0000000..fd115f6
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Models/OutlineDocumentInsight.swift
@@ -0,0 +1,15 @@
+import Foundation
+
+/// A daily/weekly activity rollup for a document, backed by `documents.insights`.
+public struct OutlineDocumentInsight: Decodable, Sendable {
+    /// Plain `YYYY-MM-DD` (format: date, not date-time) — kept as `String` since
+    /// the client's `.iso8601` decoding strategy can't parse it.
+    public let date: String
+    public let period: String
+    public let viewCount: Int
+    public let viewerCount: Int
+    public let commentCount: Int
+    public let reactionCount: Int
+    public let revisionCount: Int
+    public let editorCount: Int
+}
diff --git a/OutlineKit/Sources/OutlineKit/Models/OutlineEnvelope.swift b/OutlineKit/Sources/OutlineKit/Models/OutlineEnvelope.swift
new file mode 100644
index 0000000..5be0bed
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Models/OutlineEnvelope.swift
@@ -0,0 +1,20 @@
+import Foundation
+
+/// Outline wraps every successful RPC response as `{ "data": ..., "pagination": ... }`.
+struct OutlineEnvelope<T: Decodable>: Decodable {
+    let data: T
+    let pagination: OutlinePagination?
+}
+
+public struct OutlinePagination: Decodable, Sendable {
+    public let offset: Int
+    public let limit: Int
+    public let nextPath: String?
+}
+
+/// Outline error responses: `{ "ok": false, "error": "...", "message": "..." }`.
+struct OutlineErrorEnvelope: Decodable {
+    let ok: Bool
+    let error: String?
+    let message: String?
+}
diff --git a/OutlineKit/Sources/OutlineKit/Models/OutlineFileOperation.swift b/OutlineKit/Sources/OutlineKit/Models/OutlineFileOperation.swift
new file mode 100644
index 0000000..8e5b3cc
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Models/OutlineFileOperation.swift
@@ -0,0 +1,8 @@
+import Foundation
+
+/// A tracked async job — collection/document export runs server-side and
+/// this is the handle to check on it (progress polling isn't wrapped yet).
+public struct OutlineFileOperation: Decodable, Sendable {
+    public let id: String
+    public let state: String?
+}
diff --git a/OutlineKit/Sources/OutlineKit/Models/OutlinePin.swift b/OutlineKit/Sources/OutlineKit/Models/OutlinePin.swift
new file mode 100644
index 0000000..1637c40
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Models/OutlinePin.swift
@@ -0,0 +1,14 @@
+import Foundation
+
+/// A document pinned to the top of a collection (or the team home), backed by
+/// `pins.*`. Not in the vendored OpenAPI spec (`docs/reference/outline-openapi`)
+/// — that spec has no `Pins` tag at all — but the endpoint exists on Outline's
+/// actual server (`server/routes/api/pins.ts` upstream). Shape reconstructed
+/// from general knowledge of Outline's API, not verified against this spec;
+/// treat field names as best-effort until confirmed against a live server.
+public struct OutlinePin: Decodable, Identifiable, Sendable {
+    public let id: String
+    public let documentId: String
+    public let collectionId: String?
+    public let index: String?
+}
diff --git a/OutlineKit/Sources/OutlineKit/Models/OutlineRevision.swift b/OutlineKit/Sources/OutlineKit/Models/OutlineRevision.swift
new file mode 100644
index 0000000..cefa438
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Models/OutlineRevision.swift
@@ -0,0 +1,14 @@
+import Foundation
+
+/// A historical snapshot of a document, backed by `revisions.list`/`revisions.info`.
+/// `revisions.list` omits `data`/`text` for performance — this model only
+/// carries what's listed, not the full revision body.
+public struct OutlineRevision: Decodable, Identifiable, Sendable {
+    public let id: String
+    public let documentId: String
+    public let title: String
+    public let name: String?
+    public let icon: String?
+    public let collaborators: [OutlineUser]
+    public let createdAt: Date
+}
diff --git a/OutlineKit/Sources/OutlineKit/Models/OutlineShare.swift b/OutlineKit/Sources/OutlineKit/Models/OutlineShare.swift
new file mode 100644
index 0000000..1cb4660
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Models/OutlineShare.swift
@@ -0,0 +1,10 @@
+import Foundation
+
+/// A public share link for a document or collection, backed by `shares.*`.
+public struct OutlineShare: Decodable, Identifiable, Sendable {
+    public let id: String
+    public let documentId: String?
+    public let collectionId: String?
+    public let url: String
+    public let published: Bool
+}
diff --git a/OutlineKit/Sources/OutlineKit/Models/OutlineStar.swift b/OutlineKit/Sources/OutlineKit/Models/OutlineStar.swift
new file mode 100644
index 0000000..09f759d
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Models/OutlineStar.swift
@@ -0,0 +1,9 @@
+import Foundation
+
+/// A bookmark on a document or collection, shown in the user's sidebar.
+public struct OutlineStar: Decodable, Sendable {
+    public let id: String
+    public let index: String?
+    public let documentId: String?
+    public let collectionId: String?
+}
diff --git a/OutlineKit/Sources/OutlineKit/Models/OutlineSubscription.swift b/OutlineKit/Sources/OutlineKit/Models/OutlineSubscription.swift
new file mode 100644
index 0000000..9731f1d
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Models/OutlineSubscription.swift
@@ -0,0 +1,15 @@
+import Foundation
+
+/// A notification subscription on a document (or collection), backed by
+/// `subscriptions.*`. Same caveat as `OutlinePin`: not in the vendored
+/// OpenAPI spec — no `Subscriptions` tag exists there — but the endpoint
+/// exists on Outline's actual server (`server/routes/api/subscriptions.ts`
+/// upstream). Shape reconstructed from general knowledge, not verified
+/// against this spec; treat field names as best-effort until confirmed
+/// against a live server.
+public struct OutlineSubscription: Decodable, Identifiable, Sendable {
+    public let id: String
+    public let documentId: String?
+    public let collectionId: String?
+    public let event: String
+}
diff --git a/OutlineKit/Sources/OutlineKit/Models/OutlineTeam.swift b/OutlineKit/Sources/OutlineKit/Models/OutlineTeam.swift
new file mode 100644
index 0000000..47e6249
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Models/OutlineTeam.swift
@@ -0,0 +1,26 @@
+import Foundation
+
+public struct OutlineTeam: Codable, Identifiable, Hashable, Sendable {
+    public let id: String
+    public let name: String
+    public let avatarUrl: String?
+    public let url: String?
+    public let subdomain: String?
+    public let domain: String?
+
+    public init(
+        id: String,
+        name: String,
+        avatarUrl: String? = nil,
+        url: String? = nil,
+        subdomain: String? = nil,
+        domain: String? = nil
+    ) {
+        self.id = id
+        self.name = name
+        self.avatarUrl = avatarUrl
+        self.url = url
+        self.subdomain = subdomain
+        self.domain = domain
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Models/OutlineTemplate.swift b/OutlineKit/Sources/OutlineKit/Models/OutlineTemplate.swift
new file mode 100644
index 0000000..154cf59
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Models/OutlineTemplate.swift
@@ -0,0 +1,8 @@
+import Foundation
+
+/// Result of `documents.templatize` — the app doesn't browse/manage templates
+/// yet, so this only carries enough to confirm the action succeeded.
+public struct OutlineTemplate: Decodable, Identifiable, Sendable {
+    public let id: String
+    public let title: String
+}
diff --git a/OutlineKit/Sources/OutlineKit/Models/OutlineUser.swift b/OutlineKit/Sources/OutlineKit/Models/OutlineUser.swift
new file mode 100644
index 0000000..b85a6ca
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Models/OutlineUser.swift
@@ -0,0 +1,23 @@
+import Foundation
+
+public struct OutlineUser: Codable, Identifiable, Hashable, Sendable {
+    public let id: String
+    public let name: String
+    public let email: String?
+    public let avatarUrl: String?
+    public let role: String?
+
+    public init(
+        id: String,
+        name: String,
+        email: String? = nil,
+        avatarUrl: String? = nil,
+        role: String? = nil
+    ) {
+        self.id = id
+        self.name = name
+        self.email = email
+        self.avatarUrl = avatarUrl
+        self.role = role
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Models/OutlineView.swift b/OutlineKit/Sources/OutlineKit/Models/OutlineView.swift
new file mode 100644
index 0000000..7e87283
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Models/OutlineView.swift
@@ -0,0 +1,15 @@
+import Foundation
+
+/// A record of a user having viewed a document, backed by `views.list`.
+/// This is historical/aggregated (`firstViewedAt`/`lastViewedAt`/`count`),
+/// not live presence — there's no realtime "viewing right now" signal over
+/// REST, only over the Hocuspocus collaboration socket's awareness protocol.
+public struct OutlineView: Decodable, Identifiable, Sendable {
+    public let id: String
+    public let documentId: String
+    public let userId: String
+    public let user: OutlineUser
+    public let count: Int
+    public let firstViewedAt: Date?
+    public let lastViewedAt: Date?
+}
diff --git a/OutlineKit/Sources/OutlineKit/Networking/HTTPClient.swift b/OutlineKit/Sources/OutlineKit/Networking/HTTPClient.swift
new file mode 100644
index 0000000..f0f8024
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Networking/HTTPClient.swift
@@ -0,0 +1,22 @@
+import Foundation
+
+/// Thin seam over `URLSession` so `LiveOutlineAPIClient` can be tested without network access.
+public protocol HTTPClient: Sendable {
+    func send(_ request: URLRequest) async throws -> (Data, HTTPURLResponse)
+}
+
+public final class URLSessionHTTPClient: HTTPClient, Sendable {
+    private let session: URLSession
+
+    public init(session: URLSession = .shared) {
+        self.session = session
+    }
+
+    public func send(_ request: URLRequest) async throws -> (Data, HTTPURLResponse) {
+        let (data, response) = try await session.data(for: request)
+        guard let httpResponse = response as? HTTPURLResponse else {
+            throw OutlineAPIError.transport(URLError(.badServerResponse))
+        }
+        return (data, httpResponse)
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/CreateDocumentRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/CreateDocumentRequest.swift
new file mode 100644
index 0000000..07de5ea
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/CreateDocumentRequest.swift
@@ -0,0 +1,23 @@
+import Foundation
+
+public struct CreateDocumentRequest: Encodable, Sendable {
+    public let title: String
+    public let text: String
+    public let collectionId: String
+    public let parentDocumentId: String?
+    public let publish: Bool
+
+    public init(
+        title: String,
+        text: String,
+        collectionId: String,
+        parentDocumentId: String? = nil,
+        publish: Bool = true
+    ) {
+        self.title = title
+        self.text = text
+        self.collectionId = collectionId
+        self.parentDocumentId = parentDocumentId
+        self.publish = publish
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/CreatePinRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/CreatePinRequest.swift
new file mode 100644
index 0000000..e8bc0d7
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/CreatePinRequest.swift
@@ -0,0 +1,12 @@
+import Foundation
+
+/// See `OutlinePin` — best-effort shape, not in the vendored spec.
+public struct CreatePinRequest: Encodable, Sendable {
+    public let documentId: String
+    public let collectionId: String?
+
+    public init(documentId: String, collectionId: String? = nil) {
+        self.documentId = documentId
+        self.collectionId = collectionId
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/CreateShareRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/CreateShareRequest.swift
new file mode 100644
index 0000000..d6e918b
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/CreateShareRequest.swift
@@ -0,0 +1,11 @@
+import Foundation
+
+public struct CreateShareRequest: Encodable, Sendable {
+    public let documentId: String?
+    public let collectionId: String?
+
+    public init(documentId: String? = nil, collectionId: String? = nil) {
+        self.documentId = documentId
+        self.collectionId = collectionId
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/CreateSubscriptionRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/CreateSubscriptionRequest.swift
new file mode 100644
index 0000000..c2cf5f2
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/CreateSubscriptionRequest.swift
@@ -0,0 +1,12 @@
+import Foundation
+
+/// See `OutlineSubscription` — best-effort shape, not in the vendored spec.
+public struct CreateSubscriptionRequest: Encodable, Sendable {
+    public let documentId: String
+    public let event: String
+
+    public init(documentId: String, event: String = "documents.update") {
+        self.documentId = documentId
+        self.event = event
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/DeleteDocumentRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/DeleteDocumentRequest.swift
new file mode 100644
index 0000000..ce2dff6
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/DeleteDocumentRequest.swift
@@ -0,0 +1,11 @@
+import Foundation
+
+public struct DeleteDocumentRequest: Encodable, Sendable {
+    public let id: String
+    public let permanent: Bool
+
+    public init(id: String, permanent: Bool = false) {
+        self.id = id
+        self.permanent = permanent
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/DocumentIDRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/DocumentIDRequest.swift
new file mode 100644
index 0000000..e7bfb93
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/DocumentIDRequest.swift
@@ -0,0 +1,11 @@
+import Foundation
+
+/// Shared body shape for endpoints that take only `{ "id": ... }` —
+/// `documents.archive`, `documents.export`.
+public struct DocumentIDRequest: Encodable, Sendable {
+    public let id: String
+
+    public init(id: String) {
+        self.id = id
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/DocumentInsightsRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/DocumentInsightsRequest.swift
new file mode 100644
index 0000000..69a0699
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/DocumentInsightsRequest.swift
@@ -0,0 +1,13 @@
+import Foundation
+
+public struct DocumentInsightsRequest: Encodable, Sendable {
+    public let id: String
+    public let startDate: Date?
+    public let endDate: Date?
+
+    public init(id: String, startDate: Date? = nil, endDate: Date? = nil) {
+        self.id = id
+        self.startDate = startDate
+        self.endDate = endDate
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/DocumentSearchRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/DocumentSearchRequest.swift
new file mode 100644
index 0000000..60ee656
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/DocumentSearchRequest.swift
@@ -0,0 +1,45 @@
+import Foundation
+
+/// Full-text search across a workspace, backed by `documents.search`.
+public struct DocumentSearchRequest: Encodable, Sendable {
+    public let query: String
+    public let collectionId: String?
+    public let documentId: String?
+    public let userId: String?
+    public let statusFilter: [DocumentStatusFilter]?
+    public let dateFilter: DocumentSearchDateFilter?
+    public let sort: DocumentSearchSort?
+    public let direction: DocumentSearchDirection?
+    public let offset: Int
+    public let limit: Int
+    public let snippetMinWords: Int?
+    public let snippetMaxWords: Int?
+
+    public init(
+        query: String,
+        collectionId: String? = nil,
+        documentId: String? = nil,
+        userId: String? = nil,
+        statusFilter: [DocumentStatusFilter]? = nil,
+        dateFilter: DocumentSearchDateFilter? = nil,
+        sort: DocumentSearchSort? = nil,
+        direction: DocumentSearchDirection? = nil,
+        offset: Int = 0,
+        limit: Int = 25,
+        snippetMinWords: Int? = nil,
+        snippetMaxWords: Int? = nil
+    ) {
+        self.query = query
+        self.collectionId = collectionId
+        self.documentId = documentId
+        self.userId = userId
+        self.statusFilter = statusFilter
+        self.dateFilter = dateFilter
+        self.sort = sort
+        self.direction = direction
+        self.offset = offset
+        self.limit = limit
+        self.snippetMinWords = snippetMinWords
+        self.snippetMaxWords = snippetMaxWords
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/DocumentSearchTitlesRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/DocumentSearchTitlesRequest.swift
new file mode 100644
index 0000000..f798a34
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/DocumentSearchTitlesRequest.swift
@@ -0,0 +1,39 @@
+import Foundation
+
+/// Fast title-only search, backed by `documents.search_titles`.
+public struct DocumentSearchTitlesRequest: Encodable, Sendable {
+    public let query: String
+    public let collectionId: String?
+    public let documentId: String?
+    public let userId: String?
+    public let statusFilter: [DocumentStatusFilter]?
+    public let dateFilter: DocumentSearchDateFilter?
+    public let sort: DocumentSearchSort?
+    public let direction: DocumentSearchDirection?
+    public let offset: Int
+    public let limit: Int
+
+    public init(
+        query: String,
+        collectionId: String? = nil,
+        documentId: String? = nil,
+        userId: String? = nil,
+        statusFilter: [DocumentStatusFilter]? = nil,
+        dateFilter: DocumentSearchDateFilter? = nil,
+        sort: DocumentSearchSort? = nil,
+        direction: DocumentSearchDirection? = nil,
+        offset: Int = 0,
+        limit: Int = 25
+    ) {
+        self.query = query
+        self.collectionId = collectionId
+        self.documentId = documentId
+        self.userId = userId
+        self.statusFilter = statusFilter
+        self.dateFilter = dateFilter
+        self.sort = sort
+        self.direction = direction
+        self.offset = offset
+        self.limit = limit
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/DuplicateDocumentRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/DuplicateDocumentRequest.swift
new file mode 100644
index 0000000..ec3303b
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/DuplicateDocumentRequest.swift
@@ -0,0 +1,15 @@
+import Foundation
+
+public struct DuplicateDocumentRequest: Encodable, Sendable {
+    public let id: String
+    public let title: String?
+    public let recursive: Bool
+    public let publish: Bool
+
+    public init(id: String, title: String? = nil, recursive: Bool = true, publish: Bool = true) {
+        self.id = id
+        self.title = title
+        self.recursive = recursive
+        self.publish = publish
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/ExportCollectionRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/ExportCollectionRequest.swift
new file mode 100644
index 0000000..ebc55af
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/ExportCollectionRequest.swift
@@ -0,0 +1,17 @@
+import Foundation
+
+public enum CollectionExportFormat: String, Encodable, Sendable, CaseIterable {
+    case markdown = "outline-markdown"
+    case json
+    case html
+}
+
+public struct ExportCollectionRequest: Encodable, Sendable {
+    public let id: String
+    public let format: CollectionExportFormat
+
+    public init(id: String, format: CollectionExportFormat = .markdown) {
+        self.id = id
+        self.format = format
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/ListPinsRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/ListPinsRequest.swift
new file mode 100644
index 0000000..29dc61f
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/ListPinsRequest.swift
@@ -0,0 +1,10 @@
+import Foundation
+
+/// See `OutlinePin` — best-effort shape, not in the vendored spec.
+public struct ListPinsRequest: Encodable, Sendable {
+    public let collectionId: String?
+
+    public init(collectionId: String? = nil) {
+        self.collectionId = collectionId
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/ListRevisionsRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/ListRevisionsRequest.swift
new file mode 100644
index 0000000..66d79a1
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/ListRevisionsRequest.swift
@@ -0,0 +1,13 @@
+import Foundation
+
+public struct ListRevisionsRequest: Encodable, Sendable {
+    public let documentId: String
+    public let offset: Int
+    public let limit: Int
+
+    public init(documentId: String, offset: Int = 0, limit: Int = 25) {
+        self.documentId = documentId
+        self.offset = offset
+        self.limit = limit
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/ListStarsRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/ListStarsRequest.swift
new file mode 100644
index 0000000..b27f770
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/ListStarsRequest.swift
@@ -0,0 +1,11 @@
+import Foundation
+
+public struct ListStarsRequest: Encodable, Sendable {
+    public let offset: Int
+    public let limit: Int
+
+    public init(offset: Int = 0, limit: Int = 100) {
+        self.offset = offset
+        self.limit = limit
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/ListSubscriptionsRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/ListSubscriptionsRequest.swift
new file mode 100644
index 0000000..5348078
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/ListSubscriptionsRequest.swift
@@ -0,0 +1,12 @@
+import Foundation
+
+/// See `OutlineSubscription` — best-effort shape, not in the vendored spec.
+public struct ListSubscriptionsRequest: Encodable, Sendable {
+    public let documentId: String
+    public let event: String
+
+    public init(documentId: String, event: String = "documents.update") {
+        self.documentId = documentId
+        self.event = event
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/ListViewsRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/ListViewsRequest.swift
new file mode 100644
index 0000000..b46e51e
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/ListViewsRequest.swift
@@ -0,0 +1,9 @@
+import Foundation
+
+public struct ListViewsRequest: Encodable, Sendable {
+    public let documentId: String
+
+    public init(documentId: String) {
+        self.documentId = documentId
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/MoveDocumentRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/MoveDocumentRequest.swift
new file mode 100644
index 0000000..b87ee9e
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/MoveDocumentRequest.swift
@@ -0,0 +1,13 @@
+import Foundation
+
+public struct MoveDocumentRequest: Encodable, Sendable {
+    public let id: String
+    public let collectionId: String
+    public let parentDocumentId: String?
+
+    public init(id: String, collectionId: String, parentDocumentId: String? = nil) {
+        self.id = id
+        self.collectionId = collectionId
+        self.parentDocumentId = parentDocumentId
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/ShareInfoRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/ShareInfoRequest.swift
new file mode 100644
index 0000000..37aa05a
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/ShareInfoRequest.swift
@@ -0,0 +1,9 @@
+import Foundation
+
+public struct ShareInfoRequest: Encodable, Sendable {
+    public let documentId: String?
+
+    public init(documentId: String?) {
+        self.documentId = documentId
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/StarCollectionRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/StarCollectionRequest.swift
new file mode 100644
index 0000000..b3f3bd8
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/StarCollectionRequest.swift
@@ -0,0 +1,9 @@
+import Foundation
+
+public struct StarCollectionRequest: Encodable, Sendable {
+    public let collectionId: String
+
+    public init(collectionId: String) {
+        self.collectionId = collectionId
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/StarDocumentRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/StarDocumentRequest.swift
new file mode 100644
index 0000000..54036a4
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/StarDocumentRequest.swift
@@ -0,0 +1,9 @@
+import Foundation
+
+public struct StarDocumentRequest: Encodable, Sendable {
+    public let documentId: String
+
+    public init(documentId: String) {
+        self.documentId = documentId
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/TemplatizeDocumentRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/TemplatizeDocumentRequest.swift
new file mode 100644
index 0000000..c919668
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/TemplatizeDocumentRequest.swift
@@ -0,0 +1,13 @@
+import Foundation
+
+public struct TemplatizeDocumentRequest: Encodable, Sendable {
+    public let id: String
+    public let collectionId: String?
+    public let publish: Bool
+
+    public init(id: String, collectionId: String? = nil, publish: Bool = true) {
+        self.id = id
+        self.collectionId = collectionId
+        self.publish = publish
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/UnpublishDocumentRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/UnpublishDocumentRequest.swift
new file mode 100644
index 0000000..4d44fe6
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/UnpublishDocumentRequest.swift
@@ -0,0 +1,11 @@
+import Foundation
+
+public struct UnpublishDocumentRequest: Encodable, Sendable {
+    public let id: String
+    public let detach: Bool
+
+    public init(id: String, detach: Bool = false) {
+        self.id = id
+        self.detach = detach
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/UpdateCollectionRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/UpdateCollectionRequest.swift
new file mode 100644
index 0000000..7b094f1
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/UpdateCollectionRequest.swift
@@ -0,0 +1,17 @@
+import Foundation
+
+public struct UpdateCollectionRequest: Encodable, Sendable {
+    public let id: String
+    public let name: String?
+    public let description: String?
+
+    public init(
+        id: String,
+        name: String? = nil,
+        description: String? = nil
+    ) {
+        self.id = id
+        self.name = name
+        self.description = description
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/UpdateDocumentRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/UpdateDocumentRequest.swift
new file mode 100644
index 0000000..b7a5611
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/UpdateDocumentRequest.swift
@@ -0,0 +1,34 @@
+import Foundation
+
+public struct UpdateDocumentRequest: Encodable, Sendable {
+    public let id: String
+    public let title: String?
+    public let text: String?
+    public let append: Bool?
+    public let fullWidth: Bool?
+    public let insightsEnabled: Bool?
+    /// Not in the vendored spec's `Document`/`documents.update` shape at all
+    /// (only a workspace-level `documentEmbeds` flag exists there) — included
+    /// speculatively since the field may exist on newer self-hosted servers.
+    /// Unrecognized fields are typically ignored server-side rather than
+    /// rejected, so this is low-risk even if unsupported.
+    public let documentEmbeds: Bool?
+
+    public init(
+        id: String,
+        title: String? = nil,
+        text: String? = nil,
+        append: Bool? = nil,
+        fullWidth: Bool? = nil,
+        insightsEnabled: Bool? = nil,
+        documentEmbeds: Bool? = nil
+    ) {
+        self.id = id
+        self.title = title
+        self.text = text
+        self.append = append
+        self.fullWidth = fullWidth
+        self.insightsEnabled = insightsEnabled
+        self.documentEmbeds = documentEmbeds
+    }
+}
diff --git a/OutlineKit/Sources/OutlineKit/Requests/UpdateShareRequest.swift b/OutlineKit/Sources/OutlineKit/Requests/UpdateShareRequest.swift
new file mode 100644
index 0000000..9b9abc5
--- /dev/null
+++ b/OutlineKit/Sources/OutlineKit/Requests/UpdateShareRequest.swift
@@ -0,0 +1,11 @@
+import Foundation
+
+public struct UpdateShareRequest: Encodable, Sendable {
+    public let id: String
+    public let published: Bool
+
+    public init(id: String, published: Bool) {
+        self.id = id
+        self.published = published
+    }
+}
diff --git a/OutlineKit/Tests/OutlineKitTests/LiveOutlineAPIClientTests.swift b/OutlineKit/Tests/OutlineKitTests/LiveOutlineAPIClientTests.swift
new file mode 100644
index 0000000..82c518f
--- /dev/null
+++ b/OutlineKit/Tests/OutlineKitTests/LiveOutlineAPIClientTests.swift
@@ -0,0 +1,712 @@
+import XCTest
+@testable import OutlineKit
+
+private final class MockHTTPClient: HTTPClient, @unchecked Sendable {
+    var lastRequest: URLRequest?
+    var responseData: Data = Data()
+    var statusCode: Int = 200
+
+    func send(_ request: URLRequest) async throws -> (Data, HTTPURLResponse) {
+        lastRequest = request
+        let response = HTTPURLResponse(
+            url: request.url!,
+            statusCode: statusCode,
+            httpVersion: nil,
+            headerFields: nil
+        )!
+        return (responseData, response)
+    }
+}
+
+private final class StaticTokenStore: TokenStoring, @unchecked Sendable {
+    private var stored: String?
+
+    init(token: String? = "test-token") {
+        self.stored = token
+    }
+
+    func token() throws -> String {
+        guard let stored else { throw TokenStoreError.notFound }
+        return stored
+    }
+
+    func store(_ token: String) throws { stored = token }
+    func clear() throws { stored = nil }
+}
+
+final class LiveOutlineAPIClientTests: XCTestCase {
+    func testDeleteCollectionSucceedsOnSuccessTrue() 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.deleteCollection(id: "col-1")
+
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/collections.delete")
+    }
+
+    func testDeleteCollectionThrowsOnSuccessFalse() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "success": false }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        do {
+            try await client.deleteCollection(id: "col-1")
+            XCTFail("Expected an error when success is false")
+        } catch {
+            // expected
+        }
+    }
+
+    func testExportCollectionDecodesFileOperation() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "fileOperation": { "id": "op-1", "state": "creating" }
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let operation = try await client.exportCollection(ExportCollectionRequest(id: "col-1"))
+
+        XCTAssertEqual(operation.id, "op-1")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/collections.export")
+    }
+
+    func testStarCollectionDecodesStar() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "star-1",
+                "collectionId": "col-1",
+                "documentId": null
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let star = try await client.starCollection(StarCollectionRequest(collectionId: "col-1"))
+
+        XCTAssertEqual(star.id, "star-1")
+        XCTAssertEqual(star.collectionId, "col-1")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/stars.create")
+    }
+
+    func testSearchDocumentsDecodesContextAndRanking() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": [
+                {
+                    "context": "At Acme Inc our hiring practices are inclusive",
+                    "ranking": 1.1844109,
+                    "document": {
+                        "id": "doc-1",
+                        "title": "Welcome to Acme Inc",
+                        "text": "…",
+                        "url": "/doc/welcome-doc-1",
+                        "createdAt": "2026-01-01T00:00:00.000Z",
+                        "updatedAt": "2026-01-02T00:00:00.000Z"
+                    }
+                }
+            ]
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let results = try await client.searchDocuments(DocumentSearchRequest(query: "hiring"))
+
+        XCTAssertEqual(results.count, 1)
+        XCTAssertEqual(results[0].context, "At Acme Inc our hiring practices are inclusive")
+        XCTAssertEqual(results[0].document.title, "Welcome to Acme Inc")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/documents.search")
+    }
+
+    func testSearchDocumentTitlesReturnsDocumentsDirectly() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": [
+                {
+                    "id": "doc-1",
+                    "title": "Welcome to Acme Inc",
+                    "text": "…",
+                    "url": "/doc/welcome-doc-1",
+                    "createdAt": "2026-01-01T00:00:00.000Z",
+                    "updatedAt": "2026-01-02T00:00:00.000Z"
+                }
+            ]
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let results = try await client.searchDocumentTitles(DocumentSearchTitlesRequest(query: "Welcome"))
+
+        XCTAssertEqual(results.count, 1)
+        XCTAssertEqual(results[0].title, "Welcome to Acme Inc")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/documents.search_titles")
+    }
+
+    func testAuthInfoDecodesUserAndTeam() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "user": {
+                    "id": "123e4567-e89b-12d3-a456-426614174000",
+                    "name": "Jane Doe",
+                    "email": "hello@example.com",
+                    "role": "admin"
+                },
+                "team": {
+                    "id": "123e4567-e89b-12d3-a456-426614174000",
+                    "name": "Acme Inc",
+                    "url": "https://acme-inc.getoutline.com",
+                    "subdomain": "acme-inc"
+                }
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let auth = try await client.authInfo()
+
+        XCTAssertEqual(auth.user.name, "Jane Doe")
+        XCTAssertEqual(auth.team.name, "Acme Inc")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/auth.info")
+        XCTAssertEqual(httpClient.lastRequest?.value(forHTTPHeaderField: "Authorization"), "Bearer test-token")
+    }
+
+    func testUpdateCollectionSendsDescriptionAndDecodesResult() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "col-1",
+                "name": "Engineering",
+                "description": "Updated overview text.",
+                "createdAt": "2026-01-01T00:00:00.000Z",
+                "updatedAt": "2026-01-02T00:00:00.000Z"
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let collection = try await client.updateCollection(
+            UpdateCollectionRequest(id: "col-1", description: "Updated overview text.")
+        )
+
+        XCTAssertEqual(collection.description, "Updated overview text.")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/collections.update")
+
+        struct SentBody: Decodable {
+            let id: String
+            let description: String?
+        }
+
+        let sentBody = try XCTUnwrap(httpClient.lastRequest?.httpBody)
+        let decodedBody = try JSONDecoder().decode(SentBody.self, from: sentBody)
+        XCTAssertEqual(decodedBody.id, "col-1")
+        XCTAssertEqual(decodedBody.description, "Updated overview text.")
+    }
+
+    func testListDocumentsSendsParentDocumentIdFilter() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "data": [] }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        _ = try await client.listDocuments(collectionId: nil, parentDocumentId: "doc-1", offset: 0, limit: 100)
+
+        struct SentBody: Decodable {
+            let parentDocumentId: String?
+        }
+
+        let sentBody = try XCTUnwrap(httpClient.lastRequest?.httpBody)
+        let decodedBody = try JSONDecoder().decode(SentBody.self, from: sentBody)
+        XCTAssertEqual(decodedBody.parentDocumentId, "doc-1")
+    }
+
+    func testDocumentInfoDecodesEnvelopeAndSetsAuthHeader() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "doc-1",
+                "title": "Hello",
+                "text": "World",
+                "url": "/doc/hello-doc-1",
+                "createdAt": "2026-01-01T00:00:00.000Z",
+                "updatedAt": "2026-01-02T00:00:00.000Z"
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let document = try await client.documentInfo(id: "doc-1")
+
+        XCTAssertEqual(document.id, "doc-1")
+        XCTAssertEqual(document.title, "Hello")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/documents.info")
+        XCTAssertEqual(httpClient.lastRequest?.value(forHTTPHeaderField: "Authorization"), "Bearer test-token")
+    }
+
+    func testUnauthorizedStatusMapsToUnauthorizedError() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.statusCode = 401
+        httpClient.responseData = """
+        { "ok": false, "error": "authentication_required", "message": "Authentication required" }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        do {
+            _ = try await client.documentInfo(id: "doc-1")
+            XCTFail("Expected unauthorized error")
+        } catch OutlineAPIError.unauthorized {
+            // expected
+        }
+    }
+
+    func testStarDocumentDecodesStar() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "star-1",
+                "collectionId": null,
+                "documentId": "doc-1"
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let star = try await client.starDocument(StarDocumentRequest(documentId: "doc-1"))
+
+        XCTAssertEqual(star.documentId, "doc-1")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/stars.create")
+    }
+
+    func testDuplicateDocumentDecodesDocumentsArray() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "documents": [
+                    {
+                        "id": "doc-2",
+                        "title": "Hello (copy)",
+                        "text": "World",
+                        "url": "/doc/hello-copy-doc-2",
+                        "createdAt": "2026-01-01T00:00:00.000Z",
+                        "updatedAt": "2026-01-02T00:00:00.000Z"
+                    }
+                ]
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let documents = try await client.duplicateDocument(DuplicateDocumentRequest(id: "doc-1"))
+
+        XCTAssertEqual(documents.first?.id, "doc-2")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/documents.duplicate")
+    }
+
+    func testMoveDocumentSendsDestination() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "data": { "documents": [], "collections": [] } }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        try await client.moveDocument(MoveDocumentRequest(id: "doc-1", collectionId: "col-2", parentDocumentId: "doc-9"))
+
+        struct SentBody: Decodable {
+            let id: String
+            let collectionId: String
+            let parentDocumentId: String?
+        }
+
+        let sentBody = try XCTUnwrap(httpClient.lastRequest?.httpBody)
+        let decodedBody = try JSONDecoder().decode(SentBody.self, from: sentBody)
+        XCTAssertEqual(decodedBody.collectionId, "col-2")
+        XCTAssertEqual(decodedBody.parentDocumentId, "doc-9")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/documents.move")
+    }
+
+    func testDeleteDocumentSucceedsOnSuccessTrue() 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.deleteDocument(DeleteDocumentRequest(id: "doc-1"))
+
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/documents.delete")
+    }
+
+    func testArchiveDocumentDecodesDocument() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "doc-1",
+                "title": "Hello",
+                "text": "World",
+                "url": "/doc/hello-doc-1",
+                "createdAt": "2026-01-01T00:00:00.000Z",
+                "updatedAt": "2026-01-02T00:00:00.000Z",
+                "archivedAt": "2026-01-03T00:00:00.000Z"
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let document = try await client.archiveDocument(id: "doc-1")
+
+        XCTAssertNotNil(document.archivedAt)
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/documents.archive")
+    }
+
+    func testExportDocumentReturnsMarkdownString() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "data": "# Hello\\n\\nWorld" }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let markdown = try await client.exportDocument(id: "doc-1")
+
+        XCTAssertEqual(markdown, "# Hello\n\nWorld")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/documents.export")
+    }
+
+    func testListRevisionsDecodesRevisions() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": [
+                {
+                    "id": "rev-1",
+                    "documentId": "doc-1",
+                    "title": "Hello",
+                    "name": null,
+                    "icon": null,
+                    "collaborators": [
+                        { "id": "user-1", "name": "Jane Doe" }
+                    ],
+                    "createdAt": "2026-01-01T00:00:00.000Z"
+                }
+            ]
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let revisions = try await client.listRevisions(ListRevisionsRequest(documentId: "doc-1"))
+
+        XCTAssertEqual(revisions.first?.id, "rev-1")
+        XCTAssertEqual(revisions.first?.collaborators.first?.name, "Jane Doe")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/revisions.list")
+    }
+
+    func testDocumentInsightsDecodesRollups() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": [
+                {
+                    "date": "2026-01-01",
+                    "period": "day",
+                    "viewCount": 3,
+                    "viewerCount": 2,
+                    "commentCount": 0,
+                    "reactionCount": 0,
+                    "revisionCount": 1,
+                    "editorCount": 1
+                }
+            ]
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let insights = try await client.documentInsights(DocumentInsightsRequest(id: "doc-1"))
+
+        XCTAssertEqual(insights.first?.viewCount, 3)
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/documents.insights")
+    }
+
+    func testListStarsDecodesStarsArray() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "stars": [
+                    { "id": "star-1", "collectionId": "col-1", "documentId": null },
+                    { "id": "star-2", "collectionId": null, "documentId": "doc-1" }
+                ],
+                "documents": []
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let stars = try await client.listStars(ListStarsRequest())
+
+        XCTAssertEqual(stars.count, 2)
+        XCTAssertEqual(stars.first?.collectionId, "col-1")
+        XCTAssertEqual(stars.last?.documentId, "doc-1")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/stars.list")
+    }
+
+    func testDeleteStarSucceedsOnSuccessTrue() 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.deleteStar(id: "star-1")
+
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/stars.delete")
+    }
+
+    func testCreateShareDecodesShare() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "share-1",
+                "documentId": "doc-1",
+                "collectionId": null,
+                "url": "https://outline.example.com/s/share-1",
+                "published": false
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let share = try await client.createShare(CreateShareRequest(documentId: "doc-1"))
+
+        XCTAssertEqual(share.url, "https://outline.example.com/s/share-1")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/shares.create")
+    }
+
+    func testShareInfoReturnsNilOnNotFound() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.statusCode = 404
+        httpClient.responseData = """
+        { "ok": false, "error": "not_found", "message": "Not Found" }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let share = try await client.shareInfo(documentId: "doc-1")
+
+        XCTAssertNil(share)
+    }
+
+    func testListViewsDecodesViewsAndFiltersNilLastViewedAt() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": [
+                {
+                    "id": "view-1",
+                    "documentId": "doc-1",
+                    "userId": "user-1",
+                    "user": { "id": "user-1", "name": "Jane Doe" },
+                    "count": 3,
+                    "firstViewedAt": "2026-01-01T00:00:00.000Z",
+                    "lastViewedAt": "2026-01-02T00:00:00.000Z"
+                }
+            ]
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let views = try await client.listViews(ListViewsRequest(documentId: "doc-1"))
+
+        XCTAssertEqual(views.first?.user.name, "Jane Doe")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/views.list")
+    }
+
+    func testCreatePinDecodesPin() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "data": { "id": "pin-1", "documentId": "doc-1", "collectionId": "col-1", "index": "a" } }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let pin = try await client.createPin(CreatePinRequest(documentId: "doc-1", collectionId: "col-1"))
+
+        XCTAssertEqual(pin.id, "pin-1")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/pins.create")
+    }
+
+    func testCreateSubscriptionDecodesSubscription() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        { "data": { "id": "sub-1", "documentId": "doc-1", "collectionId": null, "event": "documents.update" } }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let subscription = try await client.createSubscription(CreateSubscriptionRequest(documentId: "doc-1"))
+
+        XCTAssertEqual(subscription.id, "sub-1")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/subscriptions.create")
+    }
+
+    func testMissingTokenThrowsTokenUnavailable() async throws {
+        let httpClient = MockHTTPClient()
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(token: nil),
+            httpClient: httpClient
+        )
+
+        do {
+            _ = try await client.documentInfo(id: "doc-1")
+            XCTFail("Expected tokenUnavailable error")
+        } catch OutlineAPIError.tokenUnavailable {
+            // expected
+        }
+    }
+}
diff --git a/Outpost.xcodeproj/project.pbxproj b/Outpost.xcodeproj/project.pbxproj
index 044723d..81fd07e 100644
--- a/Outpost.xcodeproj/project.pbxproj
+++ b/Outpost.xcodeproj/project.pbxproj
@@ -6,6 +6,13 @@
 	objectVersion = 110;
 	objects = {
 
+/* Begin PBXBuildFile section */
+		FAF99C44302CF1BD00C9949F /* OutlineKit in Frameworks */ = {isa = PBXBuildFile; productRef = FAF99C43302CF1BD00C9949F /* OutlineKit */; };
+		FAF99CAF302D120500C9949F /* MarkdownEngine in Frameworks */ = {isa = PBXBuildFile; productRef = FAF99CAE302D120500C9949F /* MarkdownEngine */; };
+		FAF99CB1302D120500C9949F /* MarkdownEngineCodeBlocks in Frameworks */ = {isa = PBXBuildFile; productRef = FAF99CB0302D120500C9949F /* MarkdownEngineCodeBlocks */; };
+		FAF99CB3302D120500C9949F /* MarkdownEngineLatex in Frameworks */ = {isa = PBXBuildFile; productRef = FAF99CB2302D120500C9949F /* MarkdownEngineLatex */; };
+/* End PBXBuildFile section */
+
 /* Begin PBXContainerItemProxy section */
 		FAF99C28302CE96200C9949F /* PBXContainerItemProxy */ = {
 			isa = PBXContainerItemProxy;
@@ -51,6 +58,10 @@
 		FAF99C15302CE96100C9949F /* Frameworks */ = {
 			isa = PBXFrameworksBuildPhase;
 			files = (
+				FAF99C44302CF1BD00C9949F /* OutlineKit in Frameworks */,
+				FAF99CB1302D120500C9949F /* MarkdownEngineCodeBlocks in Frameworks */,
+				FAF99CB3302D120500C9949F /* MarkdownEngineLatex in Frameworks */,
+				FAF99CAF302D120500C9949F /* MarkdownEngine in Frameworks */,
 			);
 		};
 		FAF99C24302CE96200C9949F /* Frameworks */ = {
@@ -103,6 +114,12 @@
 				FAF99C1A302CE96100C9949F /* Outpost */,
 			);
 			name = Outpost;
+			packageProductDependencies = (
+				FAF99C43302CF1BD00C9949F /* OutlineKit */,
+				FAF99CAE302D120500C9949F /* MarkdownEngine */,
+				FAF99CB0302D120500C9949F /* MarkdownEngineCodeBlocks */,
+				FAF99CB2302D120500C9949F /* MarkdownEngineLatex */,
+			);
 			productName = Outpost;
 			productReference = FAF99C18302CE96100C9949F /* Outpost.app */;
 			productType = "com.apple.product-type.application";
@@ -181,6 +198,10 @@
 			);
 			mainGroup = FAF99C0F302CE96100C9949F;
 			minimizedProjectReferenceProxies = 1;
+			packageReferences = (
+				FAF99C42302CF1BD00C9949F /* XCLocalSwiftPackageReference "OutlineKit" */,
+				FAF99CAD302D120500C9949F /* XCRemoteSwiftPackageReference "swift-markdown-engine" */,
+			);
 			preferredProjectObjectVersion = 77;
 			productRefGroup = FAF99C19302CE96100C9949F /* Products */;
 			projectDirPath = "";
@@ -364,6 +385,7 @@
 			buildSettings = {
 				ASSETCATALOG_COMPILER_APPICON_NAME = AppIcon;
 				ASSETCATALOG_COMPILER_GLOBAL_ACCENT_COLOR_NAME = AccentColor;
+				CODE_SIGN_ENTITLEMENTS = Outpost/Outpost.entitlements;
 				CODE_SIGN_STYLE = Automatic;
 				CURRENT_PROJECT_VERSION = 1;
 				DEVELOPMENT_TEAM = B95H74ZDY6;
@@ -386,7 +408,7 @@
 				LD_RUNPATH_SEARCH_PATHS = "@executable_path/Frameworks";
 				"LD_RUNPATH_SEARCH_PATHS[sdk=macosx*]" = "@executable_path/../Frameworks";
 				MACOSX_DEPLOYMENT_TARGET = 27.0;
-				MARKETING_VERSION = 1.0;
+				MARKETING_VERSION = 0.0.1;
 				PRODUCT_BUNDLE_IDENTIFIER = com.psmattas.Outpost;
 				PRODUCT_NAME = "$(TARGET_NAME)";
 				REGISTER_APP_GROUPS = YES;
@@ -408,6 +430,7 @@
 			buildSettings = {
 				ASSETCATALOG_COMPILER_APPICON_NAME = AppIcon;
 				ASSETCATALOG_COMPILER_GLOBAL_ACCENT_COLOR_NAME = AccentColor;
+				CODE_SIGN_ENTITLEMENTS = Outpost/Outpost.entitlements;
 				CODE_SIGN_STYLE = Automatic;
 				CURRENT_PROJECT_VERSION = 1;
 				DEVELOPMENT_TEAM = B95H74ZDY6;
@@ -430,7 +453,7 @@
 				LD_RUNPATH_SEARCH_PATHS = "@executable_path/Frameworks";
 				"LD_RUNPATH_SEARCH_PATHS[sdk=macosx*]" = "@executable_path/../Frameworks";
 				MACOSX_DEPLOYMENT_TARGET = 27.0;
-				MARKETING_VERSION = 1.0;
+				MARKETING_VERSION = 0.0.1;
 				PRODUCT_BUNDLE_IDENTIFIER = com.psmattas.Outpost;
 				PRODUCT_NAME = "$(TARGET_NAME)";
 				REGISTER_APP_GROUPS = YES;
@@ -585,6 +608,46 @@
 			defaultConfigurationName = Release;
 		};
 /* End XCConfigurationList section */
+
+/* Begin XCLocalSwiftPackageReference section */
+		FAF99C42302CF1BD00C9949F /* XCLocalSwiftPackageReference "OutlineKit" */ = {
+			isa = XCLocalSwiftPackageReference;
+			relativePath = OutlineKit;
+		};
+/* End XCLocalSwiftPackageReference section */
+
+/* Begin XCRemoteSwiftPackageReference section */
+		FAF99CAD302D120500C9949F /* XCRemoteSwiftPackageReference "swift-markdown-engine" */ = {
+			isa = XCRemoteSwiftPackageReference;
+			repositoryURL = "https://github.com/nodes-app/swift-markdown-engine";
+			requirement = {
+				kind = upToNextMajorVersion;
+				minimumVersion = 0.12.0;
+			};
+		};
+/* End XCRemoteSwiftPackageReference section */
+
+/* Begin XCSwiftPackageProductDependency section */
+		FAF99C43302CF1BD00C9949F /* OutlineKit */ = {
+			isa = XCSwiftPackageProductDependency;
+			productName = OutlineKit;
+		};
+		FAF99CAE302D120500C9949F /* MarkdownEngine */ = {
+			isa = XCSwiftPackageProductDependency;
+			package = FAF99CAD302D120500C9949F /* XCRemoteSwiftPackageReference "swift-markdown-engine" */;
+			productName = MarkdownEngine;
+		};
+		FAF99CB0302D120500C9949F /* MarkdownEngineCodeBlocks */ = {
+			isa = XCSwiftPackageProductDependency;
+			package = FAF99CAD302D120500C9949F /* XCRemoteSwiftPackageReference "swift-markdown-engine" */;
+			productName = MarkdownEngineCodeBlocks;
+		};
+		FAF99CB2302D120500C9949F /* MarkdownEngineLatex */ = {
+			isa = XCSwiftPackageProductDependency;
+			package = FAF99CAD302D120500C9949F /* XCRemoteSwiftPackageReference "swift-markdown-engine" */;
+			productName = MarkdownEngineLatex;
+		};
+/* End XCSwiftPackageProductDependency section */
 	};
 	rootObject = FAF99C10302CE96100C9949F /* Project object */;
 	validationLevel = 1;
diff --git a/Outpost.xcodeproj/project.xcworkspace/xcshareddata/swiftpm/Package.resolved b/Outpost.xcodeproj/project.xcworkspace/xcshareddata/swiftpm/Package.resolved
new file mode 100644
index 0000000..0ad3948
--- /dev/null
+++ b/Outpost.xcodeproj/project.xcworkspace/xcshareddata/swiftpm/Package.resolved
@@ -0,0 +1,33 @@
+{
+  "originHash" : "f233fa96f0c6bdcdbf87f726af38f25704f6d46a156a27dfac47541baa63bf97",
+  "pins" : [
+    {
+      "identity" : "highlighterswift",
+      "kind" : "remoteSourceControl",
+      "location" : "https://github.com/smittytone/HighlighterSwift",
+      "state" : {
+        "revision" : "fe7aae9c9b31d3b296fd3d2dd575e1a207bb29e0",
+        "version" : "3.1.0"
+      }
+    },
+    {
+      "identity" : "swift-markdown-engine",
+      "kind" : "remoteSourceControl",
+      "location" : "https://github.com/nodes-app/swift-markdown-engine",
+      "state" : {
+        "revision" : "e5f7607fc4021181056ef7a09dbb7573dc0237d9",
+        "version" : "0.12.0"
+      }
+    },
+    {
+      "identity" : "swiftmath",
+      "kind" : "remoteSourceControl",
+      "location" : "https://github.com/mgriebling/SwiftMath",
+      "state" : {
+        "revision" : "fa8244ed032f4a1ade4cb0571bf87d2f1a9fd2d7",
+        "version" : "1.7.3"
+      }
+    }
+  ],
+  "version" : 3
+}
diff --git a/Outpost.xcodeproj/xcuserdata/psmattas.xcuserdatad/xcschemes/xcschememanagement.plist b/Outpost.xcodeproj/xcuserdata/psmattas.xcuserdatad/xcschemes/xcschememanagement.plist
index 25c5dd0..e060b9d 100644
--- a/Outpost.xcodeproj/xcuserdata/psmattas.xcuserdatad/xcschemes/xcschememanagement.plist
+++ b/Outpost.xcodeproj/xcuserdata/psmattas.xcuserdatad/xcschemes/xcschememanagement.plist
@@ -7,7 +7,7 @@
 		<key>Outpost.xcscheme_^#shared#^_</key>
 		<dict>
 			<key>orderHint</key>
-			<integer>0</integer>
+			<integer>1</integer>
 		</dict>
 	</dict>
 </dict>
diff --git a/Outpost/Assets.xcassets/AppIcon.appiconset/Contents.json b/Outpost/Assets.xcassets/AppIcon.appiconset/Contents.json
index ffdfe15..6b366ba 100644
--- a/Outpost/Assets.xcassets/AppIcon.appiconset/Contents.json
+++ b/Outpost/Assets.xcassets/AppIcon.appiconset/Contents.json
@@ -1,6 +1,7 @@
 {
   "images" : [
     {
+      "filename" : "outpost-ios-1024.png",
       "idiom" : "universal",
       "platform" : "ios",
       "size" : "1024x1024"
@@ -28,51 +29,61 @@
       "size" : "1024x1024"
     },
     {
+      "filename" : "outpost 9.png",
       "idiom" : "mac",
       "scale" : "1x",
       "size" : "16x16"
     },
     {
+      "filename" : "outpost 8.png",
       "idiom" : "mac",
       "scale" : "2x",
       "size" : "16x16"
     },
     {
+      "filename" : "outpost 7.png",
       "idiom" : "mac",
       "scale" : "1x",
       "size" : "32x32"
     },
     {
+      "filename" : "outpost 6.png",
       "idiom" : "mac",
       "scale" : "2x",
       "size" : "32x32"
     },
     {
+      "filename" : "outpost 5.png",
       "idiom" : "mac",
       "scale" : "1x",
       "size" : "128x128"
     },
     {
+      "filename" : "outpost 4.png",
       "idiom" : "mac",
       "scale" : "2x",
       "size" : "128x128"
     },
     {
+      "filename" : "outpost.png",
       "idiom" : "mac",
       "scale" : "1x",
       "size" : "256x256"
     },
     {
+      "filename" : "outpost 1.png",
       "idiom" : "mac",
       "scale" : "2x",
       "size" : "256x256"
     },
     {
+      "filename" : "outpost 2.png",
       "idiom" : "mac",
       "scale" : "1x",
       "size" : "512x512"
     },
     {
+      "filename" : "outpost 3.png",
       "idiom" : "mac",
       "scale" : "2x",
       "size" : "512x512"
diff --git a/Outpost/Assets.xcassets/AppIcon.appiconset/outpost 1.png b/Outpost/Assets.xcassets/AppIcon.appiconset/outpost 1.png
new file mode 100644
index 0000000..d43057b
Binary files /dev/null and b/Outpost/Assets.xcassets/AppIcon.appiconset/outpost 1.png differ
diff --git a/Outpost/Assets.xcassets/AppIcon.appiconset/outpost 2.png b/Outpost/Assets.xcassets/AppIcon.appiconset/outpost 2.png
new file mode 100644
index 0000000..d43057b
Binary files /dev/null and b/Outpost/Assets.xcassets/AppIcon.appiconset/outpost 2.png differ
diff --git a/Outpost/Assets.xcassets/AppIcon.appiconset/outpost 3.png b/Outpost/Assets.xcassets/AppIcon.appiconset/outpost 3.png
new file mode 100644
index 0000000..5101a9b
Binary files /dev/null and b/Outpost/Assets.xcassets/AppIcon.appiconset/outpost 3.png differ
diff --git a/Outpost/Assets.xcassets/AppIcon.appiconset/outpost 4.png b/Outpost/Assets.xcassets/AppIcon.appiconset/outpost 4.png
new file mode 100644
index 0000000..6181ef8
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diff --git a/Outpost/ContentView.swift b/Outpost/ContentView.swift
index 77b60b9..57f4f38 100644
--- a/Outpost/ContentView.swift
+++ b/Outpost/ContentView.swift
@@ -1,80 +1,5 @@
-//
-//  ContentView.swift
-//  Outpost
-//
-//  Created by Puranjay Savar Mattas on 12/08/26.
-//
-
-import SwiftUI
-import SwiftData
-
-struct ContentView: View {
-    @Environment(\.modelContext) private var modelContext
-    @Query private var items: [Item]
-
-    var body: some View {
-        NavigationViewWrapper {
-            List {
-                ForEach(items) { item in
-                    NavigationLink {
-                        Text("Item at \(item.timestamp, format: Date.FormatStyle(date: .numeric, time: .standard))")
-                    } label: {
-                        Text(item.timestamp, format: Date.FormatStyle(date: .numeric, time: .standard))
-                    }
-                }
-                .onDelete(perform: deleteItems)
-            }
 #if os(macOS)
-            .navigationSplitViewColumnWidth(min: 180, ideal: 200)
-#endif
-            .toolbar {
-#if os(iOS)
-                ToolbarItem(placement: .navigationBarTrailing) {
-                    EditButton()
-                }
-#endif
-                ToolbarItem {
-                    Button(action: addItem) {
-                        Label("Add Item", systemImage: "plus")
-                    }
-                }
-            }
-        }
-    }
-
-    private func addItem() {
-        withAnimation {
-            let newItem = Item(timestamp: Date())
-            modelContext.insert(newItem)
-        }
-    }
-
-    private func deleteItems(offsets: IndexSet) {
-        withAnimation {
-            for index in offsets {
-                modelContext.delete(items[index])
-            }
-        }
-    }
-}
-
-fileprivate struct NavigationViewWrapper<Content: View>: View {
-    let content: () -> Content
-
-    var body: some View {
-#if os(macOS)
-        NavigationSplitView {
-            content()
-        } detail: {
-            Text("Select an item")
-        }
+typealias ContentView = ContentView_macOS
 #else
-        content()
+typealias ContentView = ContentView_iOS
 #endif
-    }
-}
-
-#Preview {
-    ContentView()
-        .modelContainer(for: Item.self, inMemory: true)
-}
diff --git a/Outpost/Features/About/AboutView.swift b/Outpost/Features/About/AboutView.swift
new file mode 100644
index 0000000..a797b19
--- /dev/null
+++ b/Outpost/Features/About/AboutView.swift
@@ -0,0 +1,79 @@
+#if os(macOS)
+import AppKit
+import SwiftUI
+
+struct AboutView: View {
+    private let repositoryURL = URL(string: "https://git.psmattas.com/psmattas/Outpost")!
+    private let releasesURL = URL(string: "https://git.psmattas.com/psmattas/Outpost/releases")!
+
+    private var appName: String {
+        Bundle.main.object(forInfoDictionaryKey: "CFBundleName") as? String ?? "Outpost"
+    }
+
+    /// 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`.
+    private let releaseStage = "ALPHA"
+
+    private var versionString: String {
+        let shortVersion = Bundle.main.object(forInfoDictionaryKey: "CFBundleShortVersionString") as? String ?? "0.0.1"
+        let buildNumber = Bundle.main.object(forInfoDictionaryKey: "CFBundleVersion") as? String ?? "1"
+        let stageSuffix = releaseStage.isEmpty ? "" : "-\(releaseStage)"
+        return "Version \(shortVersion)\(stageSuffix) (\(buildNumber))"
+    }
+
+    private var copyrightYear: String {
+        String(Calendar.current.component(.year, from: Date()))
+    }
+
+    var body: some View {
+        VStack(spacing: 16) {
+            // `NSImage(named: "AppIcon")` doesn't reliably resolve an App
+            // Icon asset-catalog entry on macOS — `NSApp.applicationIconImage`
+            // is the API that's actually guaranteed to match what the Dock
+            // and Finder show for the running app.
+            Image(nsImage: NSApp.applicationIconImage)
+                .resizable()
+                .frame(width: 80, height: 80)
+
+            VStack(spacing: 4) {
+                Text(appName)
+                    .font(.title2.bold())
+                Text(versionString)
+                    .font(.caption)
+                    .foregroundStyle(.secondary)
+            }
+
+            Text("A native Apple client for self-hosted Outline, built for full editing parity with the web app.")
+                .font(.callout)
+                .multilineTextAlignment(.center)
+                .foregroundStyle(.secondary)
+                .fixedSize(horizontal: false, vertical: true)
+                .frame(maxWidth: .infinity)
+
+            VStack(spacing: 10) {
+                Link(destination: repositoryURL) {
+                    Label("View Source on Git", systemImage: "link")
+                }
+                .font(.callout)
+
+                Button("Check for Updates…") {
+                    checkForUpdates()
+                }
+            }
+
+            Text("© \(copyrightYear) Puranjay Savar Mattas")
+                .font(.caption2)
+                .foregroundStyle(.tertiary)
+        }
+        .padding(32)
+        .frame(width: 320)
+    }
+
+    // No Sparkle-style in-app updater yet — this just opens the releases page
+    // on the self-hosted Gitea instance so the user can check/download manually.
+    private func checkForUpdates() {
+        NSWorkspace.shared.open(releasesURL)
+    }
+}
+#endif
diff --git a/Outpost/Features/Account/AccountFooter.swift b/Outpost/Features/Account/AccountFooter.swift
new file mode 100644
index 0000000..fdc932f
--- /dev/null
+++ b/Outpost/Features/Account/AccountFooter.swift
@@ -0,0 +1,122 @@
+#if os(macOS)
+import SwiftUI
+
+/// Uses a plain `Button` + `.popover` rather than `Menu`. A `Menu` whose label
+/// contains the avatar image reliably broke its own sizing on click (even after
+/// several hardening attempts) — that's specifically `Menu`'s AppKit-bridged
+/// label rendering, which a `Button` doesn't go through.
+struct AccountFooter: View {
+    @Environment(SessionStore.self) private var session
+    @Environment(\.openURL) private var openURL
+    @Environment(\.openWindow) private var openWindow
+    @Environment(\.openSettings) private var openSettings
+    @AppStorage("outpost.appearance") private var appearance: AppAppearance = .system
+    @State private var isMenuPresented = false
+    @State private var isShowingLogoutConfirmation = false
+    @State private var isShowingProfile = false
+
+    private let repositoryURL = URL(string: "https://git.psmattas.com/psmattas/Outpost")!
+    private let issuesURL = URL(string: "https://git.psmattas.com/psmattas/Outpost/issues")!
+
+    private var apiDocumentationURL: URL? {
+        session.serverURL?.appendingPathComponent("developers")
+    }
+
+    var body: some View {
+        Button {
+            isMenuPresented = true
+        } label: {
+            HStack(spacing: 10) {
+                AvatarBadge(avatarURL: session.userAvatarURL, size: 28, placeholderSystemImage: "person.crop.circle.fill")
+
+                VStack(alignment: .leading, spacing: 1) {
+                    Text(session.userName ?? "Signed In")
+                        .font(.subheadline.weight(.medium))
+                        .lineLimit(1)
+                    if let email = session.userEmail {
+                        Text(email)
+                            .font(.caption)
+                            .foregroundStyle(.secondary)
+                            .lineLimit(1)
+                    }
+                }
+
+                Spacer()
+            }
+            .padding(.horizontal, 12)
+            .padding(.vertical, 8)
+            .contentShape(Rectangle())
+        }
+        .buttonStyle(.plain)
+        .frame(maxWidth: .infinity)
+        .padding(.bottom, 16)
+        .popover(isPresented: $isMenuPresented, arrowEdge: .trailing) {
+            menuContent
+        }
+        .logoutConfirmationDialog(isPresented: $isShowingLogoutConfirmation, session: session)
+        .sheet(isPresented: $isShowingProfile) {
+            ProfileView()
+        }
+    }
+
+    private var menuContent: some View {
+        VStack(alignment: .leading, spacing: 2) {
+            menuItem("Keyboard Shortcuts…") { openWindow(id: "keyboard-shortcuts") }
+
+            Divider()
+
+            menuItem("Documentation") { openURL(repositoryURL) }
+            if let apiDocumentationURL {
+                menuItem("API Documentation") { openURL(apiDocumentationURL) }
+            }
+            menuItem("Changelog") { openURL(repositoryURL) }
+
+            Divider()
+
+            menuItem("Send Us Feedback") { openURL(issuesURL) }
+            menuItem("Report a Bug") { openURL(issuesURL) }
+
+            Divider()
+
+            VStack(alignment: .leading, spacing: 4) {
+                Text("Appearance")
+                    .font(.caption)
+                    .foregroundStyle(.secondary)
+                Picker("Appearance", selection: $appearance) {
+                    ForEach(AppAppearance.allCases) { option in
+                        Text(option.label).tag(option)
+                    }
+                }
+                .pickerStyle(.segmented)
+                .labelsHidden()
+            }
+            .padding(.horizontal, 6)
+            .padding(.vertical, 4)
+
+            menuItem("Profile…") { isShowingProfile = true }
+            menuItem("Preferences…") { openSettings() }
+
+            Divider()
+
+            menuItem("Log Out", role: .destructive) { isShowingLogoutConfirmation = true }
+        }
+        .padding(8)
+        .frame(width: 240)
+    }
+
+    private func menuItem(_ title: String, role: ButtonRole? = nil, action: @escaping () -> Void) -> some View {
+        Button(role: role) {
+            isMenuPresented = false
+            action()
+        } label: {
+            Text(title)
+                .frame(maxWidth: .infinity, alignment: .leading)
+        }
+        .buttonStyle(.plain)
+        .foregroundStyle(role == .destructive ? Color.red : Color.primary)
+        .padding(.vertical, 4)
+        .padding(.horizontal, 6)
+        .contentShape(Rectangle())
+    }
+}
+#endif
diff --git a/Outpost/Features/Account/KeyboardShortcutsView.swift b/Outpost/Features/Account/KeyboardShortcutsView.swift
new file mode 100644
index 0000000..2e98c6c
--- /dev/null
+++ b/Outpost/Features/Account/KeyboardShortcutsView.swift
@@ -0,0 +1,39 @@
+#if os(macOS)
+import SwiftUI
+
+struct KeyboardShortcutsView: View {
+    private struct Shortcut: Identifiable {
+        let id = UUID()
+        let action: String
+        let keys: String
+    }
+
+    private let shortcuts: [Shortcut] = [
+        Shortcut(action: "Sign In", keys: "⏎"),
+        Shortcut(action: "Preferences", keys: "⌘ ,"),
+        Shortcut(action: "Close Window", keys: "⌘ W"),
+        Shortcut(action: "Quit Outpost", keys: "⌘ Q")
+    ]
+
+    var body: some View {
+        VStack(alignment: .leading, spacing: 16) {
+            Text("Keyboard Shortcuts")
+                .font(.title3.bold())
+
+            VStack(spacing: 10) {
+                ForEach(shortcuts) { shortcut in
+                    HStack {
+                        Text(shortcut.action)
+                        Spacer()
+                        Text(shortcut.keys)
+                            .foregroundStyle(.secondary)
+                            .monospaced()
+                    }
+                }
+            }
+        }
+        .padding(24)
+        .frame(width: 280)
+    }
+}
+#endif
diff --git a/Outpost/Features/Account/PreferencesView.swift b/Outpost/Features/Account/PreferencesView.swift
new file mode 100644
index 0000000..cfe27e9
--- /dev/null
+++ b/Outpost/Features/Account/PreferencesView.swift
@@ -0,0 +1,40 @@
+#if os(macOS)
+import SwiftUI
+
+struct PreferencesView: View {
+    @Environment(SessionStore.self) private var session
+    @AppStorage("outpost.appearance") private var appearance: AppAppearance = .system
+    @State private var isShowingLogoutConfirmation = false
+
+    var body: some View {
+        Form {
+            Section("Appearance") {
+                Picker("Appearance", selection: $appearance) {
+                    ForEach(AppAppearance.allCases) { option in
+                        Text(option.label).tag(option)
+                    }
+                }
+                .pickerStyle(.segmented)
+                .labelsHidden()
+            }
+
+            Section("Account") {
+                LabeledContent("Signed in as", value: session.userName ?? "—")
+                if let email = session.userEmail {
+                    LabeledContent("Email", value: email)
+                }
+                if let teamName = session.teamName {
+                    LabeledContent("Workspace", value: teamName)
+                }
+
+                Button("Log Out…", role: .destructive) {
+                    isShowingLogoutConfirmation = true
+                }
+            }
+        }
+        .formStyle(.grouped)
+        .frame(width: 380, height: 300)
+        .logoutConfirmationDialog(isPresented: $isShowingLogoutConfirmation, session: session)
+    }
+}
+#endif
diff --git a/Outpost/Features/Account/ProfileView.swift b/Outpost/Features/Account/ProfileView.swift
new file mode 100644
index 0000000..d4907be
--- /dev/null
+++ b/Outpost/Features/Account/ProfileView.swift
@@ -0,0 +1,37 @@
+#if os(macOS)
+import SwiftUI
+
+struct ProfileView: View {
+    @Environment(SessionStore.self) private var session
+    @Environment(\.dismiss) private var dismiss
+
+    var body: some View {
+        VStack(spacing: 16) {
+            AvatarBadge(avatarURL: session.userAvatarURL, size: 64, placeholderSystemImage: "person.crop.circle.fill")
+
+            VStack(spacing: 4) {
+                Text(session.userName ?? "Unknown")
+                    .font(.title3.bold())
+                if let email = session.userEmail {
+                    Text(email)
+                        .font(.callout)
+                        .foregroundStyle(.secondary)
+                }
+            }
+
+            if let teamName = session.teamName {
+                Label(teamName, systemImage: "building.2")
+                    .font(.callout)
+                    .foregroundStyle(.secondary)
+            }
+
+            Button("Done") {
+                dismiss()
+            }
+            .keyboardShortcut(.defaultAction)
+        }
+        .padding(32)
+        .frame(width: 300)
+    }
+}
+#endif
diff --git a/Outpost/Features/Auth/AuthHeaderView.swift b/Outpost/Features/Auth/AuthHeaderView.swift
new file mode 100644
index 0000000..efa4249
--- /dev/null
+++ b/Outpost/Features/Auth/AuthHeaderView.swift
@@ -0,0 +1,31 @@
+import SwiftUI
+
+struct AuthHeaderView: View {
+    var body: some View {
+        VStack(spacing: 12) {
+            ZStack {
+                Circle()
+                    .fill(
+                        LinearGradient(
+                            colors: [Color.accentColor, Color.accentColor.opacity(0.6)],
+                            startPoint: .topLeading,
+                            endPoint: .bottomTrailing
+                        )
+                    )
+                    .frame(width: 64, height: 64)
+                Image(systemName: "text.book.closed.fill")
+                    .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")
+                    .font(.title2.bold())
+                Text("Sign in to your Outline workspace")
+                    .font(.subheadline)
+                    .foregroundStyle(.secondary)
+            }
+        }
+    }
+}
diff --git a/Outpost/Features/Auth/AuthView.swift b/Outpost/Features/Auth/AuthView.swift
new file mode 100644
index 0000000..5700d7d
--- /dev/null
+++ b/Outpost/Features/Auth/AuthView.swift
@@ -0,0 +1,5 @@
+#if os(macOS)
+typealias AuthView = AuthView_macOS
+#else
+typealias AuthView = AuthView_iOS
+#endif
diff --git a/Outpost/Features/Auth/AuthViewModel.swift b/Outpost/Features/Auth/AuthViewModel.swift
new file mode 100644
index 0000000..a2e9dc8
--- /dev/null
+++ b/Outpost/Features/Auth/AuthViewModel.swift
@@ -0,0 +1,104 @@
+import Foundation
+import Observation
+import OutlineKit
+
+enum AuthValidationError: Error {
+    case emptyURL
+    case httpNotAllowed
+    case invalidURL
+}
+
+@MainActor
+@Observable
+final class AuthViewModel {
+    struct AuthResult {
+        let serverURL: URL
+        let user: OutlineUser
+        let team: OutlineTeam
+    }
+
+    static let httpsHint = "Outline requires HTTPS. We'll add it automatically if you don't include a scheme."
+
+    var serverURLString = ""
+    var apiToken = ""
+    var isValidating = false
+    var errorMessage: String?
+
+    private let tokenStore: TokenStoring
+
+    init(tokenStore: TokenStoring = KeychainTokenStore()) {
+        self.tokenStore = tokenStore
+    }
+
+    var canSubmit: Bool {
+        !serverURLString.trimmingCharacters(in: .whitespaces).isEmpty
+            && !apiToken.trimmingCharacters(in: .whitespaces).isEmpty
+            && !isValidating
+    }
+
+    func signIn() async -> AuthResult? {
+        errorMessage = nil
+
+        let url: URL
+        do {
+            url = try Self.resolvedURL(from: serverURLString)
+        } catch {
+            errorMessage = Self.message(for: error)
+            return nil
+        }
+
+        isValidating = true
+        defer { isValidating = false }
+
+        do {
+            try tokenStore.store(apiToken)
+            let client = LiveOutlineAPIClient(
+                configuration: OutlineConfiguration(baseURL: url),
+                tokenStore: tokenStore
+            )
+            let auth = try await client.authInfo()
+            return AuthResult(serverURL: url, user: auth.user, team: auth.team)
+        } catch {
+            try? tokenStore.clear()
+            errorMessage = Self.message(for: error)
+            return nil
+        }
+    }
+
+    private static func resolvedURL(from raw: String) throws -> URL {
+        let trimmed = raw.trimmingCharacters(in: .whitespacesAndNewlines)
+        guard !trimmed.isEmpty else {
+            throw AuthValidationError.emptyURL
+        }
+
+        if trimmed.lowercased().hasPrefix("http://") {
+            throw AuthValidationError.httpNotAllowed
+        }
+
+        let withScheme = trimmed.lowercased().hasPrefix("https://") ? trimmed : "https://\(trimmed)"
+
+        guard let url = URL(string: withScheme), let host = url.host, !host.isEmpty else {
+            throw AuthValidationError.invalidURL
+        }
+        return url
+    }
+
+    private static func message(for error: Error) -> String {
+        switch error {
+        case AuthValidationError.httpNotAllowed:
+            return "HTTP is not supported. Outline requires HTTPS to protect your API token."
+        case AuthValidationError.emptyURL:
+            return "Enter your Outline server address."
+        case AuthValidationError.invalidURL:
+            return "That doesn't look like a valid server address."
+        case OutlineAPIError.unauthorized:
+            return "Invalid API token."
+        case OutlineAPIError.tokenUnavailable:
+            return "Could not access Keychain."
+        case OutlineAPIError.transport:
+            return "Could not reach server. Check the address and try again."
+        default:
+            return "Sign in failed. Please try again."
+        }
+    }
+}
diff --git a/Outpost/Features/Auth/AuthView_iOS.swift b/Outpost/Features/Auth/AuthView_iOS.swift
new file mode 100644
index 0000000..42e2684
--- /dev/null
+++ b/Outpost/Features/Auth/AuthView_iOS.swift
@@ -0,0 +1,108 @@
+#if os(iOS)
+import SwiftUI
+
+struct AuthView_iOS: View {
+    @State private var viewModel = AuthViewModel()
+    @FocusState private var focusedField: Field?
+    var onSigningIn: (AuthViewModel.AuthResult) -> Void
+
+    private enum Field {
+        case serverURL, apiToken
+    }
+
+    var body: some View {
+        ScrollView {
+            VStack(spacing: 28) {
+                AuthHeaderView()
+                    .padding(.top, 48)
+
+                VStack(spacing: 16) {
+                    VStack(alignment: .leading, spacing: 6) {
+                        fieldLabel("Server", systemImage: "globe")
+
+                        TextField("outline.example.com", text: $viewModel.serverURLString)
+                            .textFieldStyle(.plain)
+                            .padding(14)
+                            .background(.fill.tertiary, in: RoundedRectangle(cornerRadius: 12))
+                            .textInputAutocapitalization(.never)
+                            .autocorrectionDisabled()
+                            .keyboardType(.URL)
+                            .focused($focusedField, equals: .serverURL)
+                            .submitLabel(.next)
+                            .onSubmit { focusedField = .apiToken }
+
+                        Label(AuthViewModel.httpsHint, systemImage: "lock.fill")
+                            .font(.caption)
+                            .foregroundStyle(.secondary)
+                    }
+
+                    VStack(alignment: .leading, spacing: 6) {
+                        fieldLabel("API Token", systemImage: "key.fill")
+
+                        SecureField("Personal API token", text: $viewModel.apiToken)
+                            .textFieldStyle(.plain)
+                            .padding(14)
+                            .background(.fill.tertiary, in: RoundedRectangle(cornerRadius: 12))
+                            .focused($focusedField, equals: .apiToken)
+                            .submitLabel(.go)
+                            .onSubmit { submit() }
+                    }
+
+                    if let errorMessage = viewModel.errorMessage {
+                        Label(errorMessage, systemImage: "exclamationmark.triangle.fill")
+                            .font(.footnote)
+                            .foregroundStyle(.red)
+                            .frame(maxWidth: .infinity, alignment: .leading)
+                            .transition(.opacity.combined(with: .move(edge: .top)))
+                    }
+
+                    Button(action: submit) {
+                        HStack {
+                            if viewModel.isValidating {
+                                ProgressView()
+                                    .tint(.white)
+                            } else {
+                                Text("Sign In")
+                                    .fontWeight(.semibold)
+                            }
+                        }
+                        .frame(maxWidth: .infinity)
+                        .padding(.vertical, 14)
+                    }
+                    .buttonStyle(.borderedProminent)
+                    .disabled(!viewModel.canSubmit)
+                }
+                .padding(20)
+                .background(.background.secondary, in: RoundedRectangle(cornerRadius: 24))
+                .padding(.horizontal, 20)
+
+                Spacer(minLength: 24)
+            }
+        }
+        .background(
+            LinearGradient(
+                colors: [Color.accentColor.opacity(0.12), Color(.systemBackground)],
+                startPoint: .top,
+                endPoint: .bottom
+            )
+            .ignoresSafeArea()
+        )
+        .animation(.easeInOut(duration: 0.2), value: viewModel.errorMessage)
+        .animation(.easeInOut(duration: 0.2), value: viewModel.isValidating)
+    }
+
+    private func fieldLabel(_ text: String, systemImage: String) -> some View {
+        Label(text, systemImage: systemImage)
+            .font(.caption.weight(.semibold))
+            .foregroundStyle(.secondary)
+    }
+
+    private func submit() {
+        focusedField = nil
+        Task {
+            guard let result = await viewModel.signIn() else { return }
+            onSigningIn(result)
+        }
+    }
+}
+#endif
diff --git a/Outpost/Features/Auth/AuthView_macOS.swift b/Outpost/Features/Auth/AuthView_macOS.swift
new file mode 100644
index 0000000..294591d
--- /dev/null
+++ b/Outpost/Features/Auth/AuthView_macOS.swift
@@ -0,0 +1,90 @@
+#if os(macOS)
+import SwiftUI
+
+struct AuthView_macOS: View {
+    @State private var viewModel = AuthViewModel()
+    @FocusState private var focusedField: Field?
+    @State private var isShowingServerHint = false
+    var onSigningIn: (AuthViewModel.AuthResult) -> Void
+
+    private enum Field {
+        case serverURL, apiToken
+    }
+
+    var body: some View {
+        VStack(spacing: 24) {
+            AuthHeaderView()
+
+            VStack(alignment: .leading, spacing: 14) {
+                VStack(alignment: .leading, spacing: 6) {
+                    HStack(spacing: 4) {
+                        Text("Server")
+                            .font(.caption.weight(.semibold))
+                            .foregroundStyle(.secondary)
+                        Button {
+                            isShowingServerHint.toggle()
+                        } label: {
+                            Image(systemName: "info.circle")
+                                .font(.caption)
+                                .foregroundStyle(.tertiary)
+                        }
+                        .buttonStyle(.plain)
+                        .help(AuthViewModel.httpsHint)
+                        .popover(isPresented: $isShowingServerHint, arrowEdge: .bottom) {
+                            Text(AuthViewModel.httpsHint)
+                                .font(.callout)
+                                .padding()
+                                .frame(width: 240)
+                        }
+                    }
+
+                    TextField("outline.example.com", text: $viewModel.serverURLString, prompt: Text("outline.example.com"))
+                        .textFieldStyle(.roundedBorder)
+                        .focused($focusedField, equals: .serverURL)
+                        .onSubmit { focusedField = .apiToken }
+                }
+
+                VStack(alignment: .leading, spacing: 6) {
+                    Text("API Token")
+                        .font(.caption.weight(.semibold))
+                        .foregroundStyle(.secondary)
+
+                    SecureField("Personal API token", text: $viewModel.apiToken, prompt: Text("Personal API token"))
+                        .textFieldStyle(.roundedBorder)
+                        .focused($focusedField, equals: .apiToken)
+                        .onSubmit { submit() }
+                }
+
+                if let errorMessage = viewModel.errorMessage {
+                    Label(errorMessage, systemImage: "exclamationmark.triangle.fill")
+                        .font(.callout)
+                        .foregroundStyle(.red)
+                        .transition(.opacity)
+                }
+
+                HStack {
+                    Spacer()
+                    if viewModel.isValidating {
+                        ProgressView()
+                            .controlSize(.small)
+                    }
+                    Button("Sign In", action: submit)
+                        .keyboardShortcut(.defaultAction)
+                        .disabled(!viewModel.canSubmit)
+                }
+            }
+        }
+        .padding(32)
+        .frame(width: 380)
+        .animation(.easeInOut(duration: 0.2), value: viewModel.errorMessage)
+    }
+
+    private func submit() {
+        focusedField = nil
+        Task {
+            guard let result = await viewModel.signIn() else { return }
+            onSigningIn(result)
+        }
+    }
+}
+#endif
diff --git a/Outpost/Features/Collections/CollectionDocumentsOutline.swift b/Outpost/Features/Collections/CollectionDocumentsOutline.swift
new file mode 100644
index 0000000..6db03f2
--- /dev/null
+++ b/Outpost/Features/Collections/CollectionDocumentsOutline.swift
@@ -0,0 +1,471 @@
+#if os(macOS)
+import AppKit
+import SwiftUI
+import UniformTypeIdentifiers
+import OutlineKit
+
+/// Nested document outline under an expanded collection in the sidebar tree —
+/// real hierarchy via `parentDocumentId`, see DocumentNode for why that's
+/// client-side rather than `collections.documents`.
+struct CollectionDocumentsOutline: View {
+    let apiClient: OutlineAPIClient
+    @State private var viewModel: DocumentsViewModel
+    let sortOption: SidebarSortOption
+    let refreshToken: Int
+    let selectedDocumentID: String?
+    /// Full chain from root to the clicked document (inclusive) — lets the
+    /// toolbar render the real hierarchy instead of just the leaf title.
+    let onSelectDocument: ([OutlineDocument]) -> Void
+
+    private var tree: [DocumentNode] {
+        buildDocumentTree(from: viewModel.documents, sortedBy: sortOption)
+    }
+
+    init(
+        apiClient: OutlineAPIClient,
+        collection: OutlineCollection,
+        sortOption: SidebarSortOption,
+        refreshToken: Int,
+        selectedDocumentID: String?,
+        onSelectDocument: @escaping ([OutlineDocument]) -> Void
+    ) {
+        self.apiClient = apiClient
+        _viewModel = State(initialValue: DocumentsViewModel(apiClient: apiClient, collection: collection))
+        self.sortOption = sortOption
+        self.refreshToken = refreshToken
+        self.selectedDocumentID = selectedDocumentID
+        self.onSelectDocument = onSelectDocument
+    }
+
+    var body: some View {
+        Group {
+            if viewModel.isLoading && viewModel.documents.isEmpty {
+                ProgressView()
+                    .controlSize(.small)
+                    .padding(.vertical, 6)
+            } else if viewModel.documents.isEmpty {
+                Text("No documents")
+                    .font(.callout)
+                    .foregroundStyle(.secondary)
+                    .padding(.vertical, 6)
+            } else {
+                ForEach(tree) { node in
+                    DocumentNodeRow(
+                        apiClient: apiClient,
+                        node: node,
+                        depth: 0,
+                        ancestors: [],
+                        selectedDocumentID: selectedDocumentID,
+                        onSelectDocument: onSelectDocument,
+                        onDocumentsChanged: { await viewModel.load() }
+                    )
+                }
+            }
+        }
+        .task(id: refreshToken) { await viewModel.load() }
+    }
+}
+
+/// `NSSavePanel`/`NSPrintOperation`/`NSPasteboard` in the action functions
+/// below must run on the main thread — without pinning this to `@MainActor`,
+/// a `Task` launched from a menu action can resume on a background executor
+/// after its first `await`, and calling those APIs off-main is what produced
+/// the ViewBridge/`nw_connection` console spam (and worse, silent failures).
+@MainActor
+private struct DocumentNodeRow: View {
+    @Environment(StarStore.self) private var starStore
+
+    let apiClient: OutlineAPIClient
+    let node: DocumentNode
+    let depth: Int
+    /// Chain from root down to (not including) this node.
+    let ancestors: [OutlineDocument]
+    let selectedDocumentID: String?
+    let onSelectDocument: ([OutlineDocument]) -> Void
+    let onDocumentsChanged: () async -> Void
+
+    @State private var isExpanded = false
+
+    @State private var isShowingRenameAlert = false
+    @State private var renameText = ""
+    @State private var isShowingUnpublishConfirmation = false
+    @State private var isShowingArchiveConfirmation = false
+    @State private var isShowingDeleteConfirmation = false
+    @State private var isShowingMoveSheet = false
+    @State private var isShowingHistorySheet = false
+    @State private var isShowingInsightsSheet = false
+    @State private var isShowingPresentSheet = false
+    @State private var isShowingSearchSheet = false
+    @State private var actionErrorMessage: String?
+
+    private var isSelected: Bool {
+        node.id == selectedDocumentID
+    }
+
+    private func containsSelected(_ node: DocumentNode) -> Bool {
+        guard let selectedDocumentID else { return false }
+        return node.children.contains {
+            $0.id == selectedDocumentID || containsSelected($0)
+        }
+    }
+
+    var body: some View {
+        VStack(alignment: .leading, spacing: 0) {
+            HStack(spacing: 6) {
+                if node.children.isEmpty {
+                    Color.clear.frame(width: 12)
+                } else {
+                    Button {
+                        isExpanded.toggle()
+                    } label: {
+                        Image(systemName: "chevron.right")
+                            .font(.caption2.weight(.semibold))
+                            .foregroundStyle(.secondary)
+                            .rotationEffect(.degrees(isExpanded ? 90 : 0))
+                            .frame(width: 12)
+                    }
+                    .buttonStyle(.plain)
+                }
+
+                Button {
+                    onSelectDocument(ancestors + [node.document])
+                } label: {
+                    HStack(spacing: 8) {
+                        if let emoji = node.document.emoji {
+                            Text(emoji)
+                                .font(.body)
+                        } else {
+                            Image(systemName: "doc.text")
+                                .font(.callout)
+                                .foregroundStyle(.secondary)
+                        }
+                        Text(node.document.title.isEmpty ? "Untitled" : node.document.title)
+                            .font(.body)
+                            .lineLimit(1)
+
+                        Spacer(minLength: 0)
+
+                        if starStore.isStarred(documentId: node.document.id) {
+                            Image(systemName: "star.fill")
+                                .font(.caption2)
+                                .foregroundStyle(.yellow)
+                        }
+                    }
+                    .contentShape(Rectangle())
+                }
+                .buttonStyle(.plain)
+            }
+            .padding(.vertical, 6)
+            .padding(.horizontal, 4)
+            .padding(.leading, CGFloat(depth) * 16)
+            .background(
+                isSelected ? Color.accentColor.opacity(0.15) : Color.clear,
+                in: RoundedRectangle(cornerRadius: 6)
+            )
+            .contextMenu { contextMenuContent }
+
+            if isExpanded {
+                ForEach(node.children) { child in
+                    DocumentNodeRow(
+                        apiClient: apiClient,
+                        node: child,
+                        depth: depth + 1,
+                        ancestors: ancestors + [node.document],
+                        selectedDocumentID: selectedDocumentID,
+                        onSelectDocument: onSelectDocument,
+                        onDocumentsChanged: onDocumentsChanged
+                    )
+                }
+            }
+        }
+        // Reveals the selected document if it's nested under this node —
+        // both on first appearance and whenever the selection changes — but
+        // never auto-collapses on the way out, so manual expand/collapse
+        // elsewhere in the tree isn't fought.
+        .task(id: selectedDocumentID) {
+            if containsSelected(node) {
+                isExpanded = true
+            }
+        }
+        .alert("Rename Document", isPresented: $isShowingRenameAlert) {
+            TextField("Title", text: $renameText)
+            Button("Cancel", role: .cancel) {}
+            Button("Rename") {
+                Task { await rename() }
+            }
+        }
+        .confirmationDialog(
+            "Unpublish \"\(node.document.title.isEmpty ? "Untitled" : node.document.title)\"?",
+            isPresented: $isShowingUnpublishConfirmation,
+            titleVisibility: .visible
+        ) {
+            Button("Unpublish", role: .destructive) {
+                Task { await unpublish() }
+            }
+            Button("Cancel", role: .cancel) {}
+        } message: {
+            Text("This moves the document back to a draft and out of the collection.")
+        }
+        .confirmationDialog(
+            "Archive \"\(node.document.title.isEmpty ? "Untitled" : node.document.title)\"?",
+            isPresented: $isShowingArchiveConfirmation,
+            titleVisibility: .visible
+        ) {
+            Button("Archive", role: .destructive) {
+                Task { await archive() }
+            }
+            Button("Cancel", role: .cancel) {}
+        } message: {
+            Text("Archived documents are hidden from the collection but can be restored later.")
+        }
+        .confirmationDialog(
+            "Delete \"\(node.document.title.isEmpty ? "Untitled" : node.document.title)\"?",
+            isPresented: $isShowingDeleteConfirmation,
+            titleVisibility: .visible
+        ) {
+            Button("Delete", role: .destructive) {
+                Task { await delete() }
+            }
+            Button("Cancel", role: .cancel) {}
+        } message: {
+            Text("This moves the document to the trash. If not restored within 30 days it's permanently deleted.")
+        }
+        .alert("Couldn't Complete Action", isPresented: .constant(actionErrorMessage != nil)) {
+            Button("OK") { actionErrorMessage = nil }
+        } message: {
+            Text(actionErrorMessage ?? "")
+        }
+        .sheet(isPresented: $isShowingMoveSheet) {
+            MoveDocumentSheet(apiClient: apiClient, document: node.document) {
+                await onDocumentsChanged()
+            }
+        }
+        .sheet(isPresented: $isShowingHistorySheet) {
+            DocumentHistorySheet(apiClient: apiClient, document: node.document)
+        }
+        .sheet(isPresented: $isShowingInsightsSheet) {
+            DocumentInsightsSheet(apiClient: apiClient, document: node.document)
+        }
+        .sheet(isPresented: $isShowingPresentSheet) {
+            DocumentPresentSheet(apiClient: apiClient, document: node.document)
+        }
+        .sheet(isPresented: $isShowingSearchSheet) {
+            DocumentSearchSheet(apiClient: apiClient, document: node.document)
+        }
+    }
+
+    @ViewBuilder
+    private var contextMenuContent: some View {
+        Button(starStore.isStarred(documentId: node.document.id) ? "Unstar" : "Star") {
+            Task { await star() }
+        }
+        // No `subscriptions.*` endpoint in the API — nothing to back this with.
+        Button("Unsubscribe") {}
+            .disabled(true)
+
+        Divider()
+
+        // Editing isn't wired up yet anywhere in the app (Phase 1 is
+        // read-only) — this stays disabled rather than opening a half-built path.
+        Button("Edit") {}
+            .disabled(true)
+        Button("Rename…") {
+            renameText = node.document.title
+            isShowingRenameAlert = true
+        }
+        // Sharing/membership management is its own subsystem, not a one-off
+        // action — deferred rather than half-built here.
+        Button("Permissions…") {}
+            .disabled(true)
+
+        Divider()
+
+        Button("Templatize") {
+            Task { await templatize() }
+        }
+        Button("Duplicate") {
+            Task { await duplicate() }
+        }
+        Button("Unpublish") {
+            isShowingUnpublishConfirmation = true
+        }
+        Button("Archive…") {
+            isShowingArchiveConfirmation = true
+        }
+
+        Divider()
+
+        Button("Move") {
+            isShowingMoveSheet = true
+        }
+        // Multipart file upload is its own subsystem (file picker, format
+        // detection, progress) — deferred rather than half-built here.
+        Button("Import Document…") {}
+            .disabled(true)
+        Button("New Document") {
+            Task { await createChildDocument() }
+        }
+        // No `pins.*` endpoint in the API — nothing to back this with.
+        Button("Pin") {}
+            .disabled(true)
+
+        Divider()
+
+        Button("History") {
+            isShowingHistorySheet = true
+        }
+        Button("Insights") {
+            isShowingInsightsSheet = true
+        }
+        Button("Present") {
+            isShowingPresentSheet = true
+        }
+
+        Divider()
+
+        Button("Download") {
+            Task { await download() }
+        }
+        Button("Copy") {
+            Task { await copyMarkdown() }
+        }
+        Button("Print") {
+            Task { await printDocument() }
+        }
+        Button("Search in Document") {
+            isShowingSearchSheet = true
+        }
+
+        Divider()
+
+        Button("Delete…", role: .destructive) {
+            isShowingDeleteConfirmation = true
+        }
+    }
+
+    private func star() async {
+        do {
+            try await starStore.toggleDocument(node.document.id, apiClient: apiClient)
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't update the star on this document.")
+        }
+    }
+
+    private func rename() async {
+        do {
+            _ = try await apiClient.updateDocument(UpdateDocumentRequest(id: node.document.id, title: renameText))
+            await onDocumentsChanged()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't rename this document.")
+        }
+    }
+
+    private func templatize() async {
+        do {
+            _ = try await apiClient.templatizeDocument(TemplatizeDocumentRequest(id: node.document.id))
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't templatize this document.")
+        }
+    }
+
+    private func duplicate() async {
+        do {
+            _ = try await apiClient.duplicateDocument(DuplicateDocumentRequest(id: node.document.id))
+            await onDocumentsChanged()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't duplicate this document.")
+        }
+    }
+
+    private func unpublish() async {
+        do {
+            _ = try await apiClient.unpublishDocument(UnpublishDocumentRequest(id: node.document.id))
+            await onDocumentsChanged()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't unpublish this document.")
+        }
+    }
+
+    private func archive() async {
+        do {
+            _ = try await apiClient.archiveDocument(id: node.document.id)
+            await onDocumentsChanged()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't archive this document.")
+        }
+    }
+
+    private func createChildDocument() async {
+        guard let collectionId = node.document.collectionId else {
+            actionErrorMessage = "This document isn't in a collection."
+            return
+        }
+        do {
+            _ = try await apiClient.createDocument(
+                CreateDocumentRequest(
+                    title: "Untitled",
+                    text: "",
+                    collectionId: collectionId,
+                    parentDocumentId: node.document.id
+                )
+            )
+            await onDocumentsChanged()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't create a new document.")
+        }
+    }
+
+    private func delete() async {
+        do {
+            try await apiClient.deleteDocument(DeleteDocumentRequest(id: node.document.id))
+            await onDocumentsChanged()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't delete this document.")
+        }
+    }
+
+    private func download() async {
+        do {
+            let markdown = try await apiClient.exportDocument(id: node.document.id)
+            let panel = NSSavePanel()
+            panel.nameFieldStringValue = "\(node.document.title.isEmpty ? "Untitled" : node.document.title).md"
+            panel.allowedContentTypes = [.text]
+            guard panel.runModal() == .OK, let url = panel.url else { return }
+            try markdown.write(to: url, atomically: true, encoding: .utf8)
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't download this document.")
+        }
+    }
+
+    private func copyMarkdown() async {
+        do {
+            let full = try await apiClient.documentInfo(id: node.document.id)
+            let pasteboard = NSPasteboard.general
+            pasteboard.clearContents()
+            pasteboard.setString(full.text, forType: .string)
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't copy this document.")
+        }
+    }
+
+    /// No access to the reader's rendered `NSTextView` (MarkdownEngine
+    /// doesn't expose it), so this prints the raw markdown source as plain
+    /// monospaced text via a standalone `NSTextView` built just for the print
+    /// job, rather than a styled rendering of the document.
+    private func printDocument() async {
+        do {
+            let full = try await apiClient.documentInfo(id: node.document.id)
+            let textView = NSTextView(frame: NSRect(x: 0, y: 0, width: 612, height: 792))
+            textView.string = full.text
+            textView.font = .monospacedSystemFont(ofSize: 11, weight: .regular)
+
+            let operation = NSPrintOperation(view: textView)
+            operation.printInfo.horizontalPagination = .fit
+            operation.printInfo.verticalPagination = .automatic
+            operation.run()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't print this document.")
+        }
+    }
+}
+#endif
diff --git a/Outpost/Features/Collections/CollectionListContent.swift b/Outpost/Features/Collections/CollectionListContent.swift
new file mode 100644
index 0000000..c2399ab
--- /dev/null
+++ b/Outpost/Features/Collections/CollectionListContent.swift
@@ -0,0 +1,42 @@
+import SwiftUI
+import OutlineKit
+
+struct CollectionListContent: View {
+    var viewModel: CollectionsViewModel
+    let onSelect: (OutlineCollection) -> Void
+
+    var body: some View {
+        Group {
+            if viewModel.isLoading && viewModel.collections.isEmpty {
+                ProgressView()
+                    .frame(maxWidth: .infinity, maxHeight: .infinity)
+            } else if let errorMessage = viewModel.errorMessage, viewModel.collections.isEmpty {
+                ContentUnavailableView {
+                    Label("Couldn't Load Collections", systemImage: "exclamationmark.triangle")
+                } description: {
+                    Text(errorMessage)
+                } actions: {
+                    Button("Retry") {
+                        Task { await viewModel.load() }
+                    }
+                }
+            } else if viewModel.collections.isEmpty {
+                ContentUnavailableView(
+                    "No Collections",
+                    systemImage: "folder",
+                    description: Text("Collections you have access to will appear here.")
+                )
+            } else {
+                List(viewModel.collections) { collection in
+                    Button {
+                        onSelect(collection)
+                    } label: {
+                        CollectionRowView(collection: collection)
+                    }
+                    .buttonStyle(.plain)
+                }
+            }
+        }
+        .task { await viewModel.load() }
+    }
+}
diff --git a/Outpost/Features/Collections/CollectionOverviewContent.swift b/Outpost/Features/Collections/CollectionOverviewContent.swift
new file mode 100644
index 0000000..ad2fcbf
--- /dev/null
+++ b/Outpost/Features/Collections/CollectionOverviewContent.swift
@@ -0,0 +1,29 @@
+#if os(macOS)
+import SwiftUI
+import MarkdownEngine
+import OutlineKit
+
+/// Read-only for now — document/overview editing isn't wired up yet. Uses
+/// `NativeTextViewWrapper`'s own `isEditable: false`, not `.disabled(true)`:
+/// the latter blocks ALL interaction including link clicks, since
+/// `isSelectable` and link-opening both still need to work.
+struct CollectionOverviewContent: View {
+    @State private var markdown: String
+
+    init(collection: OutlineCollection) {
+        _markdown = State(initialValue: collection.description ?? "")
+    }
+
+    var body: some View {
+        ScrollView {
+            NativeTextViewWrapper(
+                text: $markdown,
+                configuration: .init(heightBehavior: .fitsContent),
+                isEditable: false
+            )
+            .padding()
+        }
+        .frame(maxWidth: .infinity, maxHeight: .infinity, alignment: .topLeading)
+    }
+}
+#endif
diff --git a/Outpost/Features/Collections/CollectionOverviewView.swift b/Outpost/Features/Collections/CollectionOverviewView.swift
new file mode 100644
index 0000000..2436a06
--- /dev/null
+++ b/Outpost/Features/Collections/CollectionOverviewView.swift
@@ -0,0 +1,189 @@
+#if os(macOS)
+import SwiftUI
+import OutlineKit
+
+struct CollectionOverviewView: View {
+    let collection: OutlineCollection
+    @State private var viewModel: DocumentsViewModel
+    @State private var selectedTab: CollectionTab = .overview
+
+    // Contextual search — "search what you're looking at" — scoped to this
+    // collection's documents. The field itself lives on the parent
+    // NavigationStack (so it survives pushing into a document); this owns
+    // only the resulting search state.
+    @State private var searchViewModel: DocumentTitleSearchViewModel
+    @Binding var searchQuery: String
+    let onOpenDocument: (OutlineDocument) -> Void
+
+    private var trimmedSearchQuery: String {
+        searchQuery.trimmingCharacters(in: .whitespacesAndNewlines)
+    }
+
+    init(
+        apiClient: OutlineAPIClient,
+        collection: OutlineCollection,
+        searchQuery: Binding<String>,
+        onOpenDocument: @escaping (OutlineDocument) -> Void
+    ) {
+        self.collection = collection
+        _viewModel = State(initialValue: DocumentsViewModel(apiClient: apiClient, collection: collection))
+        _searchViewModel = State(initialValue: DocumentTitleSearchViewModel(apiClient: apiClient, collectionId: collection.id))
+        _searchQuery = searchQuery
+        self.onOpenDocument = onOpenDocument
+    }
+
+    private var sortedDocuments: [OutlineDocument] {
+        selectedTab.sorted(viewModel.documents)
+    }
+
+    var body: some View {
+        VStack(alignment: .leading, spacing: 0) {
+            // No in-content header — the collection's icon/title live in the
+            // window toolbar now (via `ContentView_macOS`), so this doesn't
+            // duplicate it directly below.
+            if viewModel.hasRemoteChanges {
+                RemoteChangesBanner {
+                    Task { await viewModel.load() }
+                }
+            }
+
+            if trimmedSearchQuery.isEmpty {
+                tabBar
+            }
+
+            Divider()
+
+            // All branches get the same frame so switching tabs/search doesn't
+            // visibly resize/jump the content area to its own ideal size.
+            Group {
+                if !trimmedSearchQuery.isEmpty {
+                    searchResultsList
+                } else if selectedTab == .overview {
+                    CollectionOverviewContent(collection: collection)
+                } else {
+                    documentList
+                }
+            }
+            .frame(maxWidth: .infinity, maxHeight: .infinity, alignment: .topLeading)
+            // Corner spinner for reloads with stale data already on screen
+            // (remote-changes refresh, tab switch after the first load) —
+            // `documentList`'s own spinner only covers the empty-state case.
+            .overlay(alignment: .topTrailing) {
+                if viewModel.isLoading && !viewModel.documents.isEmpty {
+                    ProgressView()
+                        .controlSize(.small)
+                        .padding(12)
+                }
+            }
+        }
+        // No `.navigationTitle` here — it renders its own native title bubble,
+        // duplicating the leading toolbar item `ContentView_macOS` already
+        // shows (which also carries the collection > document hierarchy).
+        .task { await viewModel.load() }
+        .task(id: trimmedSearchQuery) {
+            try? await Task.sleep(for: .milliseconds(250))
+            guard !Task.isCancelled else { return }
+            await searchViewModel.search(query: trimmedSearchQuery)
+        }
+        .task {
+            while !Task.isCancelled {
+                try? await Task.sleep(for: .seconds(45))
+                guard !Task.isCancelled else { break }
+                await viewModel.checkForRemoteChanges()
+            }
+        }
+    }
+
+    // Spans the full window width, centered, directly under the toolbar —
+    // not a scrolling, left-aligned row anymore.
+    private var tabBar: some View {
+        HStack(spacing: 4) {
+            Spacer(minLength: 0)
+            ForEach(CollectionTab.allCases) { tab in
+                Button {
+                    selectedTab = tab
+                } label: {
+                    Text(tab.label)
+                        .font(.callout.weight(selectedTab == tab ? .semibold : .regular))
+                        .foregroundStyle(selectedTab == tab ? Color.primary : Color.secondary)
+                        .padding(.horizontal, 10)
+                        .padding(.vertical, 6)
+                        .background(
+                            selectedTab == tab ? Color.accentColor.opacity(0.15) : Color.clear,
+                            in: RoundedRectangle(cornerRadius: 6)
+                        )
+                }
+                .buttonStyle(.plain)
+            }
+            Spacer(minLength: 0)
+        }
+        .padding(.vertical, 10)
+        .frame(maxWidth: .infinity)
+    }
+
+    @ViewBuilder
+    private var documentList: some View {
+        if viewModel.isLoading && viewModel.documents.isEmpty {
+            ProgressView()
+                .frame(maxWidth: .infinity, maxHeight: .infinity)
+        } else if let errorMessage = viewModel.errorMessage, viewModel.documents.isEmpty {
+            ContentUnavailableView {
+                Label("Couldn't Load Documents", systemImage: "exclamationmark.triangle")
+            } description: {
+                Text(errorMessage)
+            } actions: {
+                Button("Retry") {
+                    Task { await viewModel.load() }
+                }
+            }
+        } else if viewModel.documents.isEmpty {
+            ContentUnavailableView(
+                "No Documents",
+                systemImage: "doc.text",
+                description: Text("Documents in \(collection.name) will appear here.")
+            )
+        } else {
+            List(sortedDocuments) { document in
+                Button {
+                    onOpenDocument(document)
+                } label: {
+                    DocumentRowView(document: document)
+                }
+                .buttonStyle(.plain)
+            }
+        }
+    }
+
+    @ViewBuilder
+    private var searchResultsList: some View {
+        if searchViewModel.isSearching && searchViewModel.results.isEmpty {
+            ProgressView()
+                .frame(maxWidth: .infinity, maxHeight: .infinity)
+        } else if let errorMessage = searchViewModel.errorMessage {
+            ContentUnavailableView {
+                Label("Search Failed", systemImage: "exclamationmark.triangle")
+            } description: {
+                Text(errorMessage)
+            }
+        } else if searchViewModel.results.isEmpty {
+            ContentUnavailableView.search(text: trimmedSearchQuery)
+        } else {
+            List(searchViewModel.results) { result in
+                Button {
+                    onOpenDocument(result.document)
+                } label: {
+                    VStack(alignment: .leading, spacing: 4) {
+                        DocumentRowView(document: result.document)
+                        Text(result.context)
+                            .font(.callout)
+                            .foregroundStyle(.secondary)
+                            .lineLimit(2)
+                    }
+                    .padding(.vertical, 2)
+                }
+                .buttonStyle(.plain)
+            }
+        }
+    }
+}
+#endif
diff --git a/Outpost/Features/Collections/CollectionRowView.swift b/Outpost/Features/Collections/CollectionRowView.swift
new file mode 100644
index 0000000..913b9e0
--- /dev/null
+++ b/Outpost/Features/Collections/CollectionRowView.swift
@@ -0,0 +1,44 @@
+import SwiftUI
+import OutlineKit
+
+struct CollectionRowView: View {
+    let collection: OutlineCollection
+
+    var body: some View {
+        Label {
+            Text(collection.name)
+        } icon: {
+            if let emoji = collection.emojiIcon {
+                Text(emoji)
+            } else if let symbolName = collection.icon.flatMap(OutlineIconMapping.sfSymbolName) {
+                Image(systemName: symbolName)
+                    .foregroundStyle(tintColor)
+            } else {
+                Image(systemName: "folder.fill")
+                    .foregroundStyle(tintColor)
+            }
+        }
+    }
+
+    private var tintColor: Color {
+        collection.color.flatMap { Color(hex: $0) } ?? .accentColor
+    }
+}
+
+private extension OutlineCollection {
+    /// Outline's `icon` field holds either a literal emoji, or a string key
+    /// into Outline's own icon set (see OutlineIconMapping) — only the former
+    /// is renderable directly, the latter needs the lookup table.
+    var emojiIcon: String? {
+        // `isEmojiPresentation` misses symbol-class emoji that default to text
+        // presentation (e.g. some picked without a variation selector) — `isEmoji`
+        // is the broader, correct check for "this scalar can be an emoji at all".
+        // Plain ASCII digits/`#`/`*` also report `isEmoji == true` (they're valid
+        // keycap-sequence bases), so exclude the ASCII range to avoid treating a
+        // literal digit or punctuation icon name as an emoji.
+        guard let icon, icon.unicodeScalars.contains(where: { $0.properties.isEmoji && $0.value > 0x7F }) else {
+            return nil
+        }
+        return icon
+    }
+}
diff --git a/Outpost/Features/Collections/CollectionTab.swift b/Outpost/Features/Collections/CollectionTab.swift
new file mode 100644
index 0000000..71f7a0d
--- /dev/null
+++ b/Outpost/Features/Collections/CollectionTab.swift
@@ -0,0 +1,45 @@
+import Foundation
+import OutlineKit
+
+/// Mirrors Outline's own top tab bar on a collection's page.
+enum CollectionTab: String, CaseIterable, Identifiable {
+    case overview
+    case documents
+    case popular
+    case recentlyUpdated
+    case recentlyPublished
+    case leastRecentlyUpdated
+    case alphabetical
+
+    var id: String { rawValue }
+
+    var label: String {
+        switch self {
+        case .overview: return "Overview"
+        case .documents: return "Documents"
+        case .popular: return "Popular"
+        case .recentlyUpdated: return "Recently Updated"
+        case .recentlyPublished: return "Recently Published"
+        case .leastRecentlyUpdated: return "Least Recently Updated"
+        case .alphabetical: return "A-Z"
+        }
+    }
+
+    /// `.popular` has no real ranking signal yet — it would need view-count /
+    /// analytics data the REST layer doesn't expose — so it falls back to the
+    /// same order as `.documents` rather than fabricating a ranking.
+    func sorted(_ documents: [OutlineDocument]) -> [OutlineDocument] {
+        switch self {
+        case .overview, .documents, .popular:
+            return documents
+        case .recentlyUpdated:
+            return documents.sorted { $0.updatedAt > $1.updatedAt }
+        case .recentlyPublished:
+            return documents.sorted { ($0.publishedAt ?? $0.createdAt) > ($1.publishedAt ?? $1.createdAt) }
+        case .leastRecentlyUpdated:
+            return documents.sorted { $0.updatedAt < $1.updatedAt }
+        case .alphabetical:
+            return documents.sorted { $0.title.localizedStandardCompare($1.title) == .orderedAscending }
+        }
+    }
+}
diff --git a/Outpost/Features/Collections/CollectionTreeRow.swift b/Outpost/Features/Collections/CollectionTreeRow.swift
new file mode 100644
index 0000000..1bd159e
--- /dev/null
+++ b/Outpost/Features/Collections/CollectionTreeRow.swift
@@ -0,0 +1,189 @@
+#if os(macOS)
+import SwiftUI
+import OutlineKit
+
+@MainActor
+struct CollectionTreeRow: View {
+    @Environment(StarStore.self) private var starStore
+
+    let apiClient: OutlineAPIClient
+    let collection: OutlineCollection
+    let isExpanded: Bool
+    let isSelected: Bool
+    let selectedDocumentID: String?
+    let onToggle: () -> Void
+    let onSelectDocument: ([OutlineDocument]) -> Void
+    let onSearchInCollection: (OutlineCollection) -> Void
+    let onCollectionsChanged: () async -> Void
+
+    @State private var sortOption: SidebarSortOption = .manual
+    @State private var documentsRefreshToken = 0
+
+    @State private var isShowingRenameAlert = false
+    @State private var renameText = ""
+    @State private var isShowingDeleteConfirmation = false
+    @State private var actionErrorMessage: String?
+
+    var body: some View {
+        VStack(alignment: .leading, spacing: 0) {
+            Button(action: onToggle) {
+                HStack(spacing: 6) {
+                    Image(systemName: "chevron.right")
+                        .font(.caption2.weight(.semibold))
+                        .foregroundStyle(.secondary)
+                        .rotationEffect(.degrees(isExpanded ? 90 : 0))
+                        .frame(width: 12)
+
+                    CollectionRowView(collection: collection)
+
+                    Spacer(minLength: 0)
+
+                    if starStore.isStarred(collectionId: collection.id) {
+                        Image(systemName: "star.fill")
+                            .font(.caption2)
+                            .foregroundStyle(.yellow)
+                    }
+                }
+                .padding(.vertical, 4)
+                .padding(.horizontal, 6)
+                .contentShape(Rectangle())
+                .background(
+                    isSelected ? Color.accentColor.opacity(0.15) : Color.clear,
+                    in: RoundedRectangle(cornerRadius: 6)
+                )
+            }
+            .buttonStyle(.plain)
+            .animation(.easeInOut(duration: 0.15), value: isExpanded)
+            .contextMenu { contextMenuContent }
+
+            if isExpanded {
+                CollectionDocumentsOutline(
+                    apiClient: apiClient,
+                    collection: collection,
+                    sortOption: sortOption,
+                    refreshToken: documentsRefreshToken,
+                    selectedDocumentID: selectedDocumentID,
+                    onSelectDocument: onSelectDocument
+                )
+                .padding(.leading, 18)
+            }
+        }
+        .alert("Rename Collection", isPresented: $isShowingRenameAlert) {
+            TextField("Name", text: $renameText)
+            Button("Cancel", role: .cancel) {}
+            Button("Rename") {
+                Task { await rename() }
+            }
+        }
+        .confirmationDialog(
+            "Delete \"\(collection.name)\"?",
+            isPresented: $isShowingDeleteConfirmation,
+            titleVisibility: .visible
+        ) {
+            Button("Delete", role: .destructive) {
+                Task { await delete() }
+            }
+            Button("Cancel", role: .cancel) {}
+        } message: {
+            Text("This deletes the collection and all of its documents. This can't be undone.")
+        }
+        .alert("Couldn't Complete Action", isPresented: .constant(actionErrorMessage != nil)) {
+            Button("OK") { actionErrorMessage = nil }
+        } message: {
+            Text(actionErrorMessage ?? "")
+        }
+    }
+
+    @ViewBuilder
+    private var contextMenuContent: some View {
+        Button(starStore.isStarred(collectionId: collection.id) ? "Unstar" : "Star") {
+            Task { await star() }
+        }
+
+        Divider()
+
+        Button("New Document") {
+            Task { await createDocument() }
+        }
+
+        Divider()
+
+        Button("Rename…") {
+            renameText = collection.name
+            isShowingRenameAlert = true
+        }
+
+        Divider()
+
+        Menu("Sort in Sidebar") {
+            Picker("Sort", selection: $sortOption) {
+                ForEach(SidebarSortOption.allCases) { option in
+                    Text(option.label).tag(option)
+                }
+            }
+        }
+
+        Divider()
+
+        Button("Export…") {
+            Task { await export() }
+        }
+
+        Button("Search in Collection") {
+            onSearchInCollection(collection)
+        }
+
+        Divider()
+
+        Button("Delete…", role: .destructive) {
+            isShowingDeleteConfirmation = true
+        }
+    }
+
+    private func star() async {
+        do {
+            try await starStore.toggleCollection(collection.id, apiClient: apiClient)
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't update the star on this collection.")
+        }
+    }
+
+    private func createDocument() async {
+        do {
+            _ = try await apiClient.createDocument(
+                CreateDocumentRequest(title: "Untitled", text: "", collectionId: collection.id)
+            )
+            documentsRefreshToken += 1
+            await onCollectionsChanged()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't create a new document.")
+        }
+    }
+
+    private func rename() async {
+        do {
+            _ = try await apiClient.updateCollection(UpdateCollectionRequest(id: collection.id, name: renameText))
+            await onCollectionsChanged()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't rename this collection.")
+        }
+    }
+
+    private func export() async {
+        do {
+            _ = try await apiClient.exportCollection(ExportCollectionRequest(id: collection.id))
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't start the export.")
+        }
+    }
+
+    private func delete() async {
+        do {
+            try await apiClient.deleteCollection(id: collection.id)
+            await onCollectionsChanged()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't delete this collection.")
+        }
+    }
+}
+#endif
diff --git a/Outpost/Features/Collections/CollectionsTreeView.swift b/Outpost/Features/Collections/CollectionsTreeView.swift
new file mode 100644
index 0000000..fe6bf27
--- /dev/null
+++ b/Outpost/Features/Collections/CollectionsTreeView.swift
@@ -0,0 +1,124 @@
+#if os(macOS)
+import SwiftUI
+import OutlineKit
+
+struct CollectionsTreeView: View {
+    @State private var viewModel: CollectionsViewModel
+    @Binding private var selectedCollection: OutlineCollection?
+    let selectedDocumentID: String?
+    @State private var expandedCollectionIDs: Set<String> = []
+    let onSelectDocument: (OutlineCollection, [OutlineDocument]) -> Void
+    let onSearchInCollection: (OutlineCollection) -> Void
+
+    init(
+        apiClient: OutlineAPIClient,
+        selectedCollection: Binding<OutlineCollection?>,
+        selectedDocumentID: String?,
+        onSelectDocument: @escaping (OutlineCollection, [OutlineDocument]) -> Void,
+        onSearchInCollection: @escaping (OutlineCollection) -> Void
+    ) {
+        _viewModel = State(initialValue: CollectionsViewModel(apiClient: apiClient))
+        _selectedCollection = selectedCollection
+        self.selectedDocumentID = selectedDocumentID
+        self.onSelectDocument = onSelectDocument
+        self.onSearchInCollection = onSearchInCollection
+    }
+
+    var body: some View {
+        VStack(spacing: 0) {
+            if viewModel.hasRemoteChanges {
+                RemoteChangesBanner {
+                    Task { await viewModel.load() }
+                }
+            }
+            content
+        }
+        .task {
+            while !Task.isCancelled {
+                try? await Task.sleep(for: .seconds(45))
+                guard !Task.isCancelled else { break }
+                await viewModel.checkForRemoteChanges()
+            }
+        }
+    }
+
+    @ViewBuilder
+    private var content: some View {
+        Group {
+            if viewModel.isLoading && viewModel.collections.isEmpty {
+                ProgressView()
+                    .frame(maxWidth: .infinity, maxHeight: .infinity)
+            } else if let errorMessage = viewModel.errorMessage, viewModel.collections.isEmpty {
+                ContentUnavailableView {
+                    Label("Couldn't Load Collections", systemImage: "exclamationmark.triangle")
+                } description: {
+                    Text(errorMessage)
+                } actions: {
+                    Button("Retry") {
+                        Task { await viewModel.load() }
+                    }
+                }
+            } else if viewModel.collections.isEmpty {
+                ContentUnavailableView(
+                    "No Collections",
+                    systemImage: "folder",
+                    description: Text("Collections you have access to will appear here.")
+                )
+            } else {
+                // Plain `ScrollView`/`LazyVStack`, not `List`: on macOS, a
+                // `List` row's context menu wins over any `.contextMenu`
+                // nested deeper inside that row's content (right-clicking a
+                // document row inside an expanded `CollectionTreeRow` showed
+                // the collection's menu instead of the document's) — every
+                // row here already does its own selection highlighting, so
+                // `List` wasn't buying anything but that bug.
+                ScrollView {
+                    LazyVStack(alignment: .leading, spacing: 2) {
+                        ForEach(viewModel.collections) { collection in
+                            CollectionTreeRow(
+                                apiClient: viewModel.apiClient,
+                                collection: collection,
+                                isExpanded: expandedCollectionIDs.contains(collection.id),
+                                isSelected: selectedCollection?.id == collection.id,
+                                selectedDocumentID: selectedDocumentID,
+                                onToggle: { toggle(collection) },
+                                onSelectDocument: { chain in onSelectDocument(collection, chain) },
+                                onSearchInCollection: onSearchInCollection,
+                                onCollectionsChanged: { await viewModel.load() }
+                            )
+                        }
+                    }
+                    .padding(.horizontal, 8)
+                    .padding(.vertical, 4)
+                }
+            }
+        }
+        .task {
+            await viewModel.load()
+            // Stand-in for Outline's own configured "Start view" — we don't have
+            // a confirmed schema for `team.preferences` to read the actual
+            // setting, so this defaults to the first collection instead of
+            // landing on an empty "No Collection Selected" placeholder.
+            if selectedCollection == nil, let first = viewModel.collections.first {
+                selectedCollection = first
+            }
+        }
+        // A document opened from outside the sidebar (detail pane's list,
+        // global search) wouldn't otherwise expand its collection here, so
+        // the highlighted row would stay hidden.
+        .task(id: selectedDocumentID) {
+            guard selectedDocumentID != nil, let selectedCollection else { return }
+            expandedCollectionIDs.insert(selectedCollection.id)
+        }
+    }
+
+    private func toggle(_ collection: OutlineCollection) {
+        selectedCollection = collection
+        if expandedCollectionIDs.contains(collection.id) {
+            expandedCollectionIDs.remove(collection.id)
+        } else {
+            expandedCollectionIDs.insert(collection.id)
+        }
+    }
+}
+#endif
diff --git a/Outpost/Features/Collections/CollectionsViewModel.swift b/Outpost/Features/Collections/CollectionsViewModel.swift
new file mode 100644
index 0000000..981706f
--- /dev/null
+++ b/Outpost/Features/Collections/CollectionsViewModel.swift
@@ -0,0 +1,49 @@
+import Foundation
+import Observation
+import OutlineKit
+
+@MainActor
+@Observable
+final class CollectionsViewModel {
+    private(set) var collections: [OutlineCollection] = []
+    var isLoading = false
+    var errorMessage: String?
+    var hasRemoteChanges = false
+
+    let apiClient: OutlineAPIClient
+
+    init(apiClient: OutlineAPIClient) {
+        self.apiClient = apiClient
+    }
+
+    func load() async {
+        isLoading = true
+        errorMessage = nil
+        defer { isLoading = false }
+
+        do {
+            collections = try await apiClient.listCollections(offset: 0, limit: 100)
+            hasRemoteChanges = false
+        } catch {
+            errorMessage = "Couldn't load collections. Check your connection and try again."
+        }
+    }
+
+    /// Fetches fresh data to compare against what's displayed, without
+    /// replacing it — `hasRemoteChanges` drives a "Refresh" banner instead of
+    /// silently swapping content (and losing scroll position/expanded state)
+    /// out from under whoever's looking at it.
+    func checkForRemoteChanges() async {
+        guard let fresh = try? await apiClient.listCollections(offset: 0, limit: 100) else { return }
+        if Self.fingerprint(fresh) != Self.fingerprint(collections) {
+            hasRemoteChanges = true
+        }
+    }
+
+    private static func fingerprint(_ collections: [OutlineCollection]) -> String {
+        collections
+            .map { "\($0.id):\($0.updatedAt.timeIntervalSince1970)" }
+            .sorted()
+            .joined(separator: "|")
+    }
+}
diff --git a/Outpost/Features/Collections/ContentView_iOS.swift b/Outpost/Features/Collections/ContentView_iOS.swift
new file mode 100644
index 0000000..ced40d3
--- /dev/null
+++ b/Outpost/Features/Collections/ContentView_iOS.swift
@@ -0,0 +1,46 @@
+#if os(iOS)
+import SwiftUI
+import OutlineKit
+
+struct ContentView_iOS: View {
+    @Environment(SessionStore.self) private var session
+
+    var body: some View {
+        NavigationStack {
+            Group {
+                if let apiClient = session.apiClient {
+                    CollectionsScreen(apiClient: apiClient)
+                } else {
+                    ContentUnavailableView("Not Signed In", systemImage: "person.crop.circle.badge.exclamationmark")
+                }
+            }
+            .navigationTitle(session.teamName ?? "Outpost")
+            .toolbar {
+                ToolbarItem(placement: .navigation) {
+                    AvatarBadge(avatarURL: session.teamAvatarURL, placeholderSystemImage: "text.book.closed.fill")
+                }
+            }
+        }
+    }
+}
+
+private struct CollectionsScreen: View {
+    @State private var viewModel: CollectionsViewModel
+    @State private var pushedCollection: OutlineCollection?
+    private let apiClient: OutlineAPIClient
+
+    init(apiClient: OutlineAPIClient) {
+        self.apiClient = apiClient
+        _viewModel = State(initialValue: CollectionsViewModel(apiClient: apiClient))
+    }
+
+    var body: some View {
+        CollectionListContent(viewModel: viewModel) { collection in
+            pushedCollection = collection
+        }
+        .navigationDestination(item: $pushedCollection) { collection in
+            DocumentsPane(apiClient: apiClient, collection: collection)
+        }
+    }
+}
+#endif
diff --git a/Outpost/Features/Collections/ContentView_macOS.swift b/Outpost/Features/Collections/ContentView_macOS.swift
new file mode 100644
index 0000000..4d650f8
--- /dev/null
+++ b/Outpost/Features/Collections/ContentView_macOS.swift
@@ -0,0 +1,242 @@
+#if os(macOS)
+import SwiftUI
+import OutlineKit
+
+struct ContentView_macOS: View {
+    @Environment(SessionStore.self) private var session
+    @State private var selectedCollection: OutlineCollection?
+    /// The real navigation stack, root to leaf — also the source of truth for
+    /// the toolbar breadcrumb, so the two can't drift out of sync.
+    @State private var documentPath: [OutlineDocument] = []
+    @State private var globalSearchQuery = ""
+    @State private var contextualSearchQuery = ""
+    @State private var isContextualSearchExpanded = false
+    @FocusState private var isContextualSearchFocused: Bool
+
+    private var trimmedGlobalQuery: String {
+        globalSearchQuery.trimmingCharacters(in: .whitespacesAndNewlines)
+    }
+
+    var body: some View {
+        NavigationSplitView {
+            VStack(spacing: 0) {
+                SidebarSearchField(text: $globalSearchQuery)
+                Divider()
+                sidebar
+                AccountFooter()
+            }
+            .navigationSplitViewColumnWidth(min: 220, ideal: 260)
+        } detail: {
+            detail
+        }
+        // Empty rather than a real value: with one, the native title rendered
+        // in the same toolbar row as the custom `.navigation` pill below,
+        // visibly duplicating it. `.windowToolbarStyle(showsTitle: false)` was
+        // tried to suppress just the native text, but it also suppressed the
+        // custom `.navigation` item itself — an empty title sidesteps both
+        // problems (Window-menu entry is blank as a result).
+        .navigationTitle("")
+        .toolbar {
+            // Per HIG: "sidebar-toggle/back controls appear at the far leading
+            // edge, followed by the view title" — this is that title, not
+            // centered. It doesn't collide with the back button because they're
+            // mutually exclusive: whenever a document's pushed (back button
+            // visible), this shows the document hierarchy instead of falling
+            // back to the workspace badge.
+            ToolbarItem(placement: .navigation) {
+                leadingToolbarContent
+            }
+            // Custom instead of `.searchable`: that modifier always renders a
+            // full-width field, but this is meant to sit alongside the other
+            // per-document toolbar buttons as a plain icon that only expands
+            // into a field once clicked.
+            ToolbarItem(placement: .primaryAction) {
+                contextualSearchField
+            }
+        }
+    }
+
+    @ViewBuilder
+    private var contextualSearchField: some View {
+        if isContextualSearchExpanded || !contextualSearchQuery.isEmpty {
+            HStack(spacing: 4) {
+                Image(systemName: "magnifyingglass")
+                    .foregroundStyle(.secondary)
+                TextField(
+                    selectedCollection.map { "Search \($0.name)" } ?? "Search",
+                    text: $contextualSearchQuery
+                )
+                .textFieldStyle(.plain)
+                .focused($isContextualSearchFocused)
+                .frame(width: 180)
+
+                if !contextualSearchQuery.isEmpty {
+                    Button {
+                        contextualSearchQuery = ""
+                    } label: {
+                        Image(systemName: "xmark.circle.fill")
+                    }
+                    .buttonStyle(.plain)
+                    .foregroundStyle(.secondary)
+                }
+            }
+            .padding(.horizontal, 8)
+            .padding(.vertical, 4)
+            .background(.fill.tertiary, in: Capsule())
+            .onChange(of: isContextualSearchFocused) { _, focused in
+                if !focused && contextualSearchQuery.isEmpty {
+                    isContextualSearchExpanded = false
+                }
+            }
+        } else {
+            Button {
+                isContextualSearchExpanded = true
+                Task { @MainActor in isContextualSearchFocused = true }
+            } label: {
+                Image(systemName: "magnifyingglass")
+            }
+        }
+    }
+
+    @ViewBuilder
+    private var leadingToolbarContent: some View {
+        Group {
+            if !trimmedGlobalQuery.isEmpty {
+                HStack(spacing: 6) {
+                    Image(systemName: "magnifyingglass")
+                    Text("Search")
+                }
+            } else if !documentPath.isEmpty, let selectedCollection {
+                // Collection → every ancestor (icon only) → current document
+                // (icon + full title) — ancestors stay icon-only so a deep
+                // chain doesn't blow out the toolbar width.
+                HStack(spacing: 6) {
+                    CollectionRowView(collection: selectedCollection)
+
+                    ForEach(Array(documentPath.enumerated()), id: \.element.id) { index, document in
+                        Image(systemName: "chevron.right")
+                            .font(.caption2.weight(.semibold))
+                            .foregroundStyle(.tertiary)
+
+                        if let emoji = document.emoji {
+                            Text(emoji)
+                        } else {
+                            Image(systemName: "doc.text")
+                        }
+
+                        if index == documentPath.count - 1 {
+                            Text(document.title.isEmpty ? "Untitled" : document.title)
+                                .lineLimit(1)
+                        }
+                    }
+                }
+            } else if let selectedCollection {
+                CollectionRowView(collection: selectedCollection)
+            } else {
+                HStack(spacing: 8) {
+                    AvatarBadge(avatarURL: session.teamAvatarURL, placeholderSystemImage: "text.book.closed.fill")
+                    Text(session.teamName ?? "Outpost")
+                        .lineLimit(1)
+                }
+            }
+        }
+        .font(.headline)
+        .padding(.horizontal, 10)
+        .padding(.vertical, 4)
+        .background(.fill.tertiary, in: Capsule())
+    }
+
+    @ViewBuilder
+    private var sidebar: some View {
+        if let apiClient = session.apiClient {
+            CollectionsTreeView(
+                apiClient: apiClient,
+                selectedCollection: $selectedCollection,
+                selectedDocumentID: documentPath.last?.id,
+                onSelectDocument: selectDocumentChain,
+                onSearchInCollection: searchInCollection
+            )
+        } else {
+            ContentUnavailableView("Not Signed In", systemImage: "person.crop.circle.badge.exclamationmark")
+        }
+    }
+
+    private func searchInCollection(_ collection: OutlineCollection) {
+        globalSearchQuery = ""
+        selectedCollection = collection
+        isContextualSearchExpanded = true
+        Task { @MainActor in
+            isContextualSearchFocused = true
+        }
+    }
+
+    /// Sidebar clicks (which know the real ancestor chain via DocumentNode):
+    /// replaces the whole stack with `chain`, so the toolbar shows full
+    /// hierarchy immediately rather than just the leaf.
+    private func selectDocumentChain(_ collection: OutlineCollection, _ chain: [OutlineDocument]) {
+        selectedCollection = collection
+        replaceDocumentPath(with: chain)
+    }
+
+    /// Flat-list / search-result clicks: no known ancestors, single-level push.
+    private func openDocument(_ document: OutlineDocument) {
+        replaceDocumentPath(with: [document])
+    }
+
+    /// Replacing `path` with a same-size array can silently fail to update
+    /// NavigationStack on macOS — popping to empty and pushing again as two
+    /// separate state updates (so SwiftUI processes them as two render
+    /// passes) is the reliable version of the same operation. Appending
+    /// (e.g. opening a sub-document from within the reader) doesn't hit this
+    /// and can mutate `documentPath` directly.
+    private func replaceDocumentPath(with chain: [OutlineDocument]) {
+        documentPath = []
+        Task { @MainActor in
+            documentPath = chain
+        }
+    }
+
+    @ViewBuilder
+    private var detail: some View {
+        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) {
+                Group {
+                    if !trimmedGlobalQuery.isEmpty {
+                        GlobalSearchResultsView(apiClient: apiClient, query: trimmedGlobalQuery, onOpenDocument: openDocument)
+                    } else if let selectedCollection {
+                        CollectionOverviewView(
+                            apiClient: apiClient,
+                            collection: selectedCollection,
+                            searchQuery: $contextualSearchQuery,
+                            onOpenDocument: openDocument
+                        )
+                    } else {
+                        ContentUnavailableView(
+                            "No Collection Selected",
+                            systemImage: "sidebar.left",
+                            description: Text("Choose a collection to see its documents.")
+                        )
+                    }
+                }
+                .navigationDestination(for: OutlineDocument.self) { document in
+                    DocumentReaderView(
+                        apiClient: apiClient,
+                        document: document,
+                        onOpenChild: { child in documentPath.append(child) },
+                        onDeleted: {
+                            if !documentPath.isEmpty {
+                                documentPath.removeLast()
+                            }
+                        }
+                    )
+                }
+            }
+            .id(trimmedGlobalQuery.isEmpty ? (selectedCollection?.id ?? "none") : "search")
+        } else {
+            ContentUnavailableView("Not Signed In", systemImage: "person.crop.circle.badge.exclamationmark")
+        }
+    }
+}
+#endif
diff --git a/Outpost/Features/Collections/DocumentHistorySheet.swift b/Outpost/Features/Collections/DocumentHistorySheet.swift
new file mode 100644
index 0000000..1e370eb
--- /dev/null
+++ b/Outpost/Features/Collections/DocumentHistorySheet.swift
@@ -0,0 +1,76 @@
+#if os(macOS)
+import SwiftUI
+import OutlineKit
+
+/// Read-only revision list, backed by `revisions.list`. No diff/restore view —
+/// `revisions.list` omits body content for performance, and restoring is a
+/// bigger follow-up feature, not a one-off action.
+@MainActor
+struct DocumentHistorySheet: View {
+    @Environment(\.dismiss) private var dismiss
+
+    let apiClient: OutlineAPIClient
+    let document: OutlineDocument
+
+    @State private var revisions: [OutlineRevision] = []
+    @State private var isLoading = false
+    @State private var errorMessage: String?
+
+    var body: some View {
+        VStack(alignment: .leading, spacing: 0) {
+            HStack {
+                Text("History")
+                    .font(.headline)
+                Spacer()
+                Button("Done") { dismiss() }
+            }
+            .padding()
+
+            Divider()
+
+            Group {
+                if isLoading && revisions.isEmpty {
+                    ProgressView().frame(maxWidth: .infinity, maxHeight: .infinity)
+                } else if let errorMessage {
+                    ContentUnavailableView {
+                        Label("Couldn't Load History", systemImage: "exclamationmark.triangle")
+                    } description: {
+                        Text(errorMessage)
+                    }
+                } else if revisions.isEmpty {
+                    ContentUnavailableView("No Revisions Yet", systemImage: "clock")
+                } else {
+                    List(revisions) { revision in
+                        VStack(alignment: .leading, spacing: 2) {
+                            Text(revision.title.isEmpty ? "Untitled" : revision.title)
+                                .font(.body)
+                            HStack(spacing: 4) {
+                                Text(revision.createdAt, format: .dateTime.day().month().year().hour().minute())
+                                if let author = revision.collaborators.first?.name {
+                                    Text("\u{2022} \(author)")
+                                }
+                            }
+                            .font(.caption)
+                            .foregroundStyle(.secondary)
+                        }
+                        .padding(.vertical, 2)
+                    }
+                }
+            }
+            .frame(maxWidth: .infinity, maxHeight: .infinity)
+        }
+        .frame(width: 420, height: 420)
+        .task { await load() }
+    }
+
+    private func load() async {
+        isLoading = true
+        defer { isLoading = false }
+        do {
+            revisions = try await apiClient.listRevisions(ListRevisionsRequest(documentId: document.id))
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Couldn't load revision history.")
+        }
+    }
+}
+#endif
diff --git a/Outpost/Features/Collections/DocumentInsightsSheet.swift b/Outpost/Features/Collections/DocumentInsightsSheet.swift
new file mode 100644
index 0000000..e401596
--- /dev/null
+++ b/Outpost/Features/Collections/DocumentInsightsSheet.swift
@@ -0,0 +1,100 @@
+#if os(macOS)
+import SwiftUI
+import OutlineKit
+
+/// Backed by `documents.insights` — server returns an error if insights
+/// aren't enabled on the document, surfaced like any other load failure.
+@MainActor
+struct DocumentInsightsSheet: View {
+    @Environment(\.dismiss) private var dismiss
+
+    let apiClient: OutlineAPIClient
+    let document: OutlineDocument
+
+    @State private var rollups: [OutlineDocumentInsight] = []
+    @State private var isLoading = false
+    @State private var errorMessage: String?
+
+    private var totalViews: Int { rollups.reduce(0) { $0 + $1.viewCount } }
+    private var totalViewers: Int { rollups.reduce(0) { $0 + $1.viewerCount } }
+    private var totalComments: Int { rollups.reduce(0) { $0 + $1.commentCount } }
+
+    var body: some View {
+        VStack(alignment: .leading, spacing: 0) {
+            HStack {
+                Text("Insights")
+                    .font(.headline)
+                Spacer()
+                Button("Done") { dismiss() }
+            }
+            .padding()
+
+            Divider()
+
+            Group {
+                if isLoading && rollups.isEmpty {
+                    ProgressView().frame(maxWidth: .infinity, maxHeight: .infinity)
+                } else if let errorMessage {
+                    ContentUnavailableView {
+                        Label("Couldn't Load Insights", systemImage: "exclamationmark.triangle")
+                    } description: {
+                        Text(errorMessage)
+                    }
+                } else {
+                    VStack(alignment: .leading, spacing: 16) {
+                        HStack(spacing: 24) {
+                            statColumn("Views", totalViews)
+                            statColumn("Viewers", totalViewers)
+                            statColumn("Comments", totalComments)
+                        }
+
+                        Text("Last 30 days, by day")
+                            .font(.caption.weight(.semibold))
+                            .foregroundStyle(.secondary)
+
+                        if rollups.isEmpty {
+                            Text("No activity in this window.")
+                                .font(.callout)
+                                .foregroundStyle(.secondary)
+                        } else {
+                            List(rollups, id: \.date) { rollup in
+                                HStack {
+                                    Text(rollup.date)
+                                    Spacer()
+                                    Text("\(rollup.viewCount) views \u{00B7} \(rollup.viewerCount) viewers")
+                                        .foregroundStyle(.secondary)
+                                }
+                                .font(.callout)
+                            }
+                        }
+                    }
+                    .padding()
+                }
+            }
+            .frame(maxWidth: .infinity, maxHeight: .infinity)
+        }
+        .frame(width: 420, height: 420)
+        .task { await load() }
+    }
+
+    private func statColumn(_ label: String, _ value: Int) -> some View {
+        VStack(alignment: .leading, spacing: 2) {
+            Text("\(value)")
+                .font(.title2.weight(.semibold))
+            Text(label)
+                .font(.caption)
+                .foregroundStyle(.secondary)
+        }
+    }
+
+    private func load() async {
+        isLoading = true
+        defer { isLoading = false }
+        do {
+            rollups = try await apiClient.documentInsights(DocumentInsightsRequest(id: document.id))
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Couldn't load insights for this document.")
+        }
+    }
+}
+#endif
diff --git a/Outpost/Features/Collections/DocumentListContent.swift b/Outpost/Features/Collections/DocumentListContent.swift
new file mode 100644
index 0000000..3ee4c9d
--- /dev/null
+++ b/Outpost/Features/Collections/DocumentListContent.swift
@@ -0,0 +1,37 @@
+import SwiftUI
+import OutlineKit
+
+struct DocumentListContent: View {
+    var viewModel: DocumentsViewModel
+
+    var body: some View {
+        Group {
+            if viewModel.isLoading && viewModel.documents.isEmpty {
+                ProgressView()
+                    .frame(maxWidth: .infinity, maxHeight: .infinity)
+            } else if let errorMessage = viewModel.errorMessage, viewModel.documents.isEmpty {
+                ContentUnavailableView {
+                    Label("Couldn't Load Documents", systemImage: "exclamationmark.triangle")
+                } description: {
+                    Text(errorMessage)
+                } actions: {
+                    Button("Retry") {
+                        Task { await viewModel.load() }
+                    }
+                }
+            } else if viewModel.documents.isEmpty {
+                ContentUnavailableView(
+                    "No Documents",
+                    systemImage: "doc.text",
+                    description: Text("Documents in \(viewModel.collection.name) will appear here.")
+                )
+            } else {
+                List(viewModel.documents) { document in
+                    DocumentRowView(document: document)
+                }
+            }
+        }
+        .navigationTitle(viewModel.collection.name)
+        .task { await viewModel.load() }
+    }
+}
diff --git a/Outpost/Features/Collections/DocumentNode.swift b/Outpost/Features/Collections/DocumentNode.swift
new file mode 100644
index 0000000..d66d7b2
--- /dev/null
+++ b/Outpost/Features/Collections/DocumentNode.swift
@@ -0,0 +1,26 @@
+import Foundation
+import OutlineKit
+
+/// Reconstructs the real document hierarchy client-side from `parentDocumentId`.
+/// `documents.list` already returns the full flat set for a collection
+/// (including children, not just roots), so no separate tree-shaped endpoint
+/// is needed — `collections.documents` exists and returns exactly this shape,
+/// but its `NavigationNode` carries no emoji/timestamps, which would break
+/// per-row icons and date-based sidebar sorting.
+struct DocumentNode: Identifiable {
+    let document: OutlineDocument
+    let children: [DocumentNode]
+    var id: String { document.id }
+}
+
+func buildDocumentTree(from documents: [OutlineDocument], sortedBy sort: SidebarSortOption) -> [DocumentNode] {
+    let byParent = Dictionary(grouping: documents, by: { $0.parentDocumentId })
+
+    func makeNodes(parentId: String?) -> [DocumentNode] {
+        sort.sorted(byParent[parentId] ?? []).map { document in
+            DocumentNode(document: document, children: makeNodes(parentId: document.id))
+        }
+    }
+
+    return makeNodes(parentId: nil)
+}
diff --git a/Outpost/Features/Collections/DocumentPresentSheet.swift b/Outpost/Features/Collections/DocumentPresentSheet.swift
new file mode 100644
index 0000000..5c1fc5a
--- /dev/null
+++ b/Outpost/Features/Collections/DocumentPresentSheet.swift
@@ -0,0 +1,83 @@
+#if os(macOS)
+import SwiftUI
+import MarkdownEngine
+import OutlineKit
+
+/// Distraction-free reading view — no toolbar/sidebar chrome, larger type.
+/// Presentation is just a bigger render of the same markdown, not a real
+/// slide-by-slide deck (Outline's own "Present" isn't slide-based either).
+@MainActor
+struct DocumentPresentSheet: View {
+    @Environment(\.dismiss) private var dismiss
+
+    let apiClient: OutlineAPIClient
+    let document: OutlineDocument
+
+    @State private var text: String
+    @State private var isLoading = false
+    @State private var errorMessage: String?
+
+    init(apiClient: OutlineAPIClient, document: OutlineDocument) {
+        self.apiClient = apiClient
+        self.document = document
+        _text = State(initialValue: document.text)
+    }
+
+    var body: some View {
+        ZStack(alignment: .topTrailing) {
+            if isLoading && text.isEmpty {
+                ProgressView().frame(maxWidth: .infinity, maxHeight: .infinity)
+            } else if let errorMessage {
+                ContentUnavailableView {
+                    Label("Couldn't Load Document", systemImage: "exclamationmark.triangle")
+                } description: {
+                    Text(errorMessage)
+                }
+            } else {
+                ScrollView {
+                    VStack(alignment: .leading) {
+                        if let emoji = document.emoji {
+                            Text(emoji).font(.system(size: 48))
+                        }
+                        Text(document.title.isEmpty ? "Untitled" : document.title)
+                            .font(.system(size: 34, weight: .bold))
+                            .padding(.bottom, 8)
+                        NativeTextViewWrapper(
+                            text: $text,
+                            configuration: .init(heightBehavior: .fitsContent),
+                            isEditable: false
+                        )
+                        .font(.system(size: 18))
+                    }
+                    .frame(maxWidth: 720, alignment: .leading)
+                    .padding(48)
+                    .frame(maxWidth: .infinity)
+                }
+            }
+
+            Button {
+                dismiss()
+            } label: {
+                Image(systemName: "xmark.circle.fill")
+                    .font(.title2)
+                    .foregroundStyle(.secondary)
+            }
+            .buttonStyle(.plain)
+            .padding(20)
+        }
+        .frame(minWidth: 800, minHeight: 600)
+        .background(.background)
+        .task { await load() }
+    }
+
+    private func load() async {
+        isLoading = true
+        defer { isLoading = false }
+        do {
+            text = try await apiClient.documentInfo(id: document.id).text
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Couldn't load this document.")
+        }
+    }
+}
+#endif
diff --git a/Outpost/Features/Collections/DocumentReaderView.swift b/Outpost/Features/Collections/DocumentReaderView.swift
new file mode 100644
index 0000000..cbd8786
--- /dev/null
+++ b/Outpost/Features/Collections/DocumentReaderView.swift
@@ -0,0 +1,483 @@
+#if os(macOS)
+import AppKit
+import SwiftUI
+import UniformTypeIdentifiers
+import MarkdownEngine
+import OutlineKit
+
+/// `NSSavePanel`/`NSPrintOperation`/`NSPasteboard` in the action functions
+/// below must run on the main thread — see the identical note on
+/// `DocumentNodeRow` in `CollectionDocumentsOutline.swift`.
+@MainActor
+struct DocumentReaderView: View {
+    @Environment(SessionStore.self) private var session
+    @Environment(StarStore.self) private var starStore
+
+    @State private var viewModel: DocumentReaderViewModel
+    let apiClient: OutlineAPIClient
+    let document: OutlineDocument
+    /// Pushes a genuine new stack entry (not a reset+replace) — the back
+    /// button then correctly returns to this document, not the collection.
+    let onOpenChild: (OutlineDocument) -> Void
+    /// Called after Delete/Archive/Unpublish succeed — the document is no
+    /// longer visible in the collection it was opened from, so the reader
+    /// pops itself off the navigation stack.
+    let onDeleted: () -> Void
+
+    @State private var isShowingUnpublishConfirmation = false
+    @State private var isShowingArchiveConfirmation = false
+    @State private var isShowingDeleteConfirmation = false
+    @State private var isShowingMoveSheet = false
+    @State private var isShowingHistorySheet = false
+    @State private var isShowingInsightsSheet = false
+    @State private var isShowingPresentSheet = false
+    @State private var isShowingSearchSheet = false
+    @State private var isShowingShareSheet = false
+    @State private var actionErrorMessage: String?
+
+    init(
+        apiClient: OutlineAPIClient,
+        document: OutlineDocument,
+        onOpenChild: @escaping (OutlineDocument) -> Void,
+        onDeleted: @escaping () -> Void
+    ) {
+        self.apiClient = apiClient
+        self.document = document
+        _viewModel = State(initialValue: DocumentReaderViewModel(apiClient: apiClient, document: document))
+        self.onOpenChild = onOpenChild
+        self.onDeleted = onDeleted
+    }
+
+    var body: some View {
+        ScrollView {
+            VStack(alignment: .leading, spacing: 12) {
+                if viewModel.isEditing {
+                    TextField("Title", text: $viewModel.title)
+                        .font(.largeTitle.weight(.bold))
+                        .textFieldStyle(.plain)
+                }
+
+                if viewModel.isLoading && viewModel.text.isEmpty {
+                    ProgressView()
+                        .frame(maxWidth: .infinity)
+                } else if let errorMessage = viewModel.errorMessage {
+                    ContentUnavailableView {
+                        Label("Couldn't Load Document", systemImage: "exclamationmark.triangle")
+                    } description: {
+                        Text(errorMessage)
+                    } actions: {
+                        Button("Retry") {
+                            Task { await viewModel.loadFullContent() }
+                        }
+                    }
+                } else {
+                    NativeTextViewWrapper(
+                        text: $viewModel.text,
+                        configuration: .init(heightBehavior: .fitsContent),
+                        isEditable: viewModel.isEditing
+                    )
+
+                    if !viewModel.children.isEmpty {
+                        childrenSection
+                    }
+                }
+            }
+            .padding()
+            .frame(maxWidth: viewModel.isFullWidth ? .infinity : 900)
+            .frame(maxWidth: .infinity)
+        }
+        .overlay(alignment: .topTrailing) {
+            if viewModel.isLoading && !viewModel.text.isEmpty {
+                ProgressView()
+                    .controlSize(.small)
+                    .padding(12)
+            }
+        }
+        // No `.navigationTitle` here either — same reason as CollectionOverviewView.
+        .toolbar {
+            ToolbarItemGroup(placement: .primaryAction) {
+                viewerAvatars
+                Button {
+                    isShowingShareSheet = true
+                } label: {
+                    Image(systemName: "square.and.arrow.up")
+                }
+                .help("Share")
+
+                Button {
+                    Task { await viewModel.toggleEditing() }
+                } label: {
+                    if viewModel.isSaving {
+                        ProgressView().controlSize(.small)
+                    } else {
+                        Text(viewModel.isEditing ? "Done" : "Edit")
+                    }
+                }
+                .disabled(viewModel.isSaving)
+
+                Button {
+                    Task { await createChildDocument() }
+                } label: {
+                    Image(systemName: "doc.badge.plus")
+                }
+                .help("New Document")
+
+                Menu {
+                    menuContent
+                } label: {
+                    Image(systemName: "ellipsis.circle")
+                }
+            }
+        }
+        .task { await viewModel.loadFullContent() }
+        .task {
+            await viewModel.loadPinAndSubscriptionState()
+        }
+        .task {
+            while !Task.isCancelled {
+                await viewModel.loadViewers()
+                try? await Task.sleep(for: .seconds(20))
+            }
+        }
+        .confirmationDialog(
+            "Unpublish \"\(viewModel.title.isEmpty ? "Untitled" : viewModel.title)\"?",
+            isPresented: $isShowingUnpublishConfirmation,
+            titleVisibility: .visible
+        ) {
+            Button("Unpublish", role: .destructive) {
+                Task { await unpublish() }
+            }
+            Button("Cancel", role: .cancel) {}
+        } message: {
+            Text("This moves the document back to a draft and out of the collection.")
+        }
+        .confirmationDialog(
+            "Archive \"\(viewModel.title.isEmpty ? "Untitled" : viewModel.title)\"?",
+            isPresented: $isShowingArchiveConfirmation,
+            titleVisibility: .visible
+        ) {
+            Button("Archive", role: .destructive) {
+                Task { await archive() }
+            }
+            Button("Cancel", role: .cancel) {}
+        } message: {
+            Text("Archived documents are hidden from the collection but can be restored later.")
+        }
+        .confirmationDialog(
+            "Delete \"\(viewModel.title.isEmpty ? "Untitled" : viewModel.title)\"?",
+            isPresented: $isShowingDeleteConfirmation,
+            titleVisibility: .visible
+        ) {
+            Button("Delete", role: .destructive) {
+                Task { await delete() }
+            }
+            Button("Cancel", role: .cancel) {}
+        } message: {
+            Text("This moves the document to the trash. If not restored within 30 days it's permanently deleted.")
+        }
+        .alert("Couldn't Complete Action", isPresented: .constant(actionErrorMessage != nil)) {
+            Button("OK") { actionErrorMessage = nil }
+        } message: {
+            Text(actionErrorMessage ?? "")
+        }
+        .sheet(isPresented: $isShowingMoveSheet) {
+            MoveDocumentSheet(apiClient: apiClient, document: document) {
+                onDeleted()
+            }
+        }
+        .sheet(isPresented: $isShowingHistorySheet) {
+            DocumentHistorySheet(apiClient: apiClient, document: document)
+        }
+        .sheet(isPresented: $isShowingInsightsSheet) {
+            DocumentInsightsSheet(apiClient: apiClient, document: document)
+        }
+        .sheet(isPresented: $isShowingPresentSheet) {
+            DocumentPresentSheet(apiClient: apiClient, document: document)
+        }
+        .sheet(isPresented: $isShowingSearchSheet) {
+            DocumentSearchSheet(apiClient: apiClient, document: document)
+        }
+        .sheet(isPresented: $isShowingShareSheet) {
+            DocumentShareSheet(apiClient: apiClient, documentId: viewModel.documentId)
+        }
+    }
+
+    @ViewBuilder
+    private var viewerAvatars: some View {
+        if !viewModel.viewers.isEmpty {
+            HStack(spacing: -6) {
+                ForEach(viewModel.viewers.prefix(5)) { viewer in
+                    AvatarBadge(
+                        avatarURL: viewer.user.avatarUrl.flatMap { URL(string: $0, relativeTo: session.serverURL)?.absoluteURL },
+                        size: 20
+                    )
+                    .overlay(Circle().stroke(.background, lineWidth: 1.5))
+                    .help(Text(viewer.user.name))
+                }
+            }
+            .padding(.trailing, 4)
+        }
+    }
+
+    private var childrenSection: some View {
+        VStack(alignment: .leading, spacing: 8) {
+            Divider()
+                .padding(.vertical, 4)
+
+            Text("Sub-documents")
+                .font(.caption.weight(.semibold))
+                .foregroundStyle(.secondary)
+
+            ForEach(viewModel.children) { child in
+                Button {
+                    onOpenChild(child)
+                } label: {
+                    DocumentRowView(document: child)
+                }
+                .buttonStyle(.plain)
+                .padding(.vertical, 4)
+
+                if child.id != viewModel.children.last?.id {
+                    Divider()
+                }
+            }
+        }
+    }
+
+    @ViewBuilder
+    private var menuContent: some View {
+        Button(starStore.isStarred(documentId: viewModel.documentId) ? "Unstar" : "Star") {
+            Task { await star() }
+        }
+        Button(viewModel.isSubscribed ? "Unsubscribe" : "Subscribe") {
+            Task { await toggleSubscription() }
+        }
+
+        Divider()
+
+        Button(viewModel.isEditing ? "Done Editing" : "Edit") {
+            Task { await viewModel.toggleEditing() }
+        }
+        // Sharing/membership management is its own subsystem, not a one-off
+        // action — deferred rather than half-built here.
+        Button("Permissions…") {}
+            .disabled(true)
+
+        Divider()
+
+        Button("Templatize") {
+            Task { await templatize() }
+        }
+        Button("Duplicate") {
+            Task { await duplicate() }
+        }
+        Button("Unpublish") {
+            isShowingUnpublishConfirmation = true
+        }
+        Button("Archive…") {
+            isShowingArchiveConfirmation = true
+        }
+
+        Divider()
+
+        Button("Move") {
+            isShowingMoveSheet = true
+        }
+        // Multipart file upload is its own subsystem — deferred rather than
+        // half-built here.
+        Button("Import Document…") {}
+            .disabled(true)
+        Button("New Document") {
+            Task { await createChildDocument() }
+        }
+        Button(viewModel.isPinned ? "Unpin" : "Pin") {
+            Task { await togglePin() }
+        }
+
+        Divider()
+
+        Button("History") {
+            isShowingHistorySheet = true
+        }
+        Button("Insights") {
+            isShowingInsightsSheet = true
+        }
+        Button("Present") {
+            isShowingPresentSheet = true
+        }
+
+        Divider()
+
+        Button("Download") {
+            Task { await download() }
+        }
+        Button("Copy") {
+            Task { await copyMarkdown() }
+        }
+        Button("Print") {
+            Task { await printDocument() }
+        }
+        Button("Search in Document") {
+            isShowingSearchSheet = true
+        }
+
+        Divider()
+
+        Button("Enable Viewer Insights") {
+            Task { await enableInsights() }
+        }
+        Button("Enable Embeds") {
+            Task { await enableEmbeds() }
+        }
+        Button(viewModel.isFullWidth ? "Default Width" : "Full Width") {
+            Task { await toggleFullWidth() }
+        }
+
+        Divider()
+
+        Button("Delete…", role: .destructive) {
+            isShowingDeleteConfirmation = true
+        }
+    }
+
+    private func star() async {
+        do {
+            try await starStore.toggleDocument(viewModel.documentId, apiClient: apiClient)
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't update the star on this document.")
+        }
+    }
+
+    private func togglePin() async {
+        do {
+            try await viewModel.togglePin()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't update pin state.")
+        }
+    }
+
+    private func toggleSubscription() async {
+        do {
+            try await viewModel.toggleSubscription()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't update subscription state.")
+        }
+    }
+
+    private func toggleFullWidth() async {
+        do {
+            try await viewModel.toggleFullWidth()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't change document width.")
+        }
+    }
+
+    private func enableInsights() async {
+        do {
+            try await viewModel.enableViewerInsights()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't enable viewer insights.")
+        }
+    }
+
+    private func enableEmbeds() async {
+        do {
+            try await viewModel.enableEmbeds()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't enable embeds.")
+        }
+    }
+
+    private func templatize() async {
+        do {
+            _ = try await apiClient.templatizeDocument(TemplatizeDocumentRequest(id: viewModel.documentId))
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't templatize this document.")
+        }
+    }
+
+    private func duplicate() async {
+        do {
+            _ = try await apiClient.duplicateDocument(DuplicateDocumentRequest(id: viewModel.documentId))
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't duplicate this document.")
+        }
+    }
+
+    private func unpublish() async {
+        do {
+            _ = try await apiClient.unpublishDocument(UnpublishDocumentRequest(id: viewModel.documentId))
+            onDeleted()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't unpublish this document.")
+        }
+    }
+
+    private func archive() async {
+        do {
+            _ = try await apiClient.archiveDocument(id: viewModel.documentId)
+            onDeleted()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't archive this document.")
+        }
+    }
+
+    private func delete() async {
+        do {
+            try await apiClient.deleteDocument(DeleteDocumentRequest(id: viewModel.documentId))
+            onDeleted()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't delete this document.")
+        }
+    }
+
+    private func createChildDocument() async {
+        guard let collectionId = viewModel.collectionId else {
+            actionErrorMessage = "This document isn't in a collection."
+            return
+        }
+        do {
+            let child = try await apiClient.createDocument(
+                CreateDocumentRequest(title: "Untitled", text: "", collectionId: collectionId, parentDocumentId: viewModel.documentId)
+            )
+            onOpenChild(child)
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't create a new document.")
+        }
+    }
+
+    private func download() async {
+        do {
+            let markdown = try await apiClient.exportDocument(id: viewModel.documentId)
+            let panel = NSSavePanel()
+            panel.nameFieldStringValue = "\(viewModel.title.isEmpty ? "Untitled" : viewModel.title).md"
+            panel.allowedContentTypes = [.text]
+            guard panel.runModal() == .OK, let url = panel.url else { return }
+            try markdown.write(to: url, atomically: true, encoding: .utf8)
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't download this document.")
+        }
+    }
+
+    private func copyMarkdown() async {
+        let pasteboard = NSPasteboard.general
+        pasteboard.clearContents()
+        pasteboard.setString(viewModel.text, forType: .string)
+    }
+
+    /// No access to the reader's rendered `NSTextView` (MarkdownEngine
+    /// doesn't expose it), so this prints the raw markdown source as plain
+    /// monospaced text via a standalone `NSTextView` built just for the print
+    /// job, rather than a styled rendering of the document.
+    private func printDocument() async {
+        let textView = NSTextView(frame: NSRect(x: 0, y: 0, width: 612, height: 792))
+        textView.string = viewModel.text
+        textView.font = .monospacedSystemFont(ofSize: 11, weight: .regular)
+
+        let operation = NSPrintOperation(view: textView)
+        operation.printInfo.horizontalPagination = .fit
+        operation.printInfo.verticalPagination = .automatic
+        operation.run()
+    }
+}
+#endif
diff --git a/Outpost/Features/Collections/DocumentReaderViewModel.swift b/Outpost/Features/Collections/DocumentReaderViewModel.swift
new file mode 100644
index 0000000..47bc3c2
--- /dev/null
+++ b/Outpost/Features/Collections/DocumentReaderViewModel.swift
@@ -0,0 +1,181 @@
+import Foundation
+import Observation
+import OutlineKit
+
+@MainActor
+@Observable
+final class DocumentReaderViewModel {
+    var title: String
+    var emoji: String?
+    var text: String
+    var collectionId: String?
+    var isFullWidth = false
+    var children: [OutlineDocument] = []
+    var isLoading = false
+    var errorMessage: String?
+
+    var isEditing = false
+    var isSaving = false
+    var saveErrorMessage: String?
+
+    /// Recent viewers, `views.list` filtered to entries that actually have a
+    /// `lastViewedAt` — this is historical/aggregated view data, not live
+    /// "viewing right now" presence (that needs the Hocuspocus collaboration
+    /// socket's awareness protocol, which isn't wired up yet).
+    private(set) var viewers: [OutlineView] = []
+
+    private(set) var isPinned = false
+    private var pinId: String?
+    private(set) var isSubscribed = false
+    private var subscriptionId: String?
+    private(set) var share: OutlineShare?
+
+    let documentId: String
+    private let apiClient: OutlineAPIClient
+
+    init(apiClient: OutlineAPIClient, document: OutlineDocument) {
+        self.apiClient = apiClient
+        self.documentId = document.id
+        self.title = document.title
+        self.emoji = document.emoji
+        self.text = document.text
+        self.collectionId = document.collectionId
+        self.isFullWidth = document.fullWidth ?? false
+    }
+
+    /// The list endpoint's copy of a document isn't guaranteed to be the full,
+    /// current body — always re-fetch via `documents.info` when actually opened.
+    func loadFullContent() async {
+        isLoading = true
+        errorMessage = nil
+        defer { isLoading = false }
+
+        do {
+            let full = try await apiClient.documentInfo(id: documentId)
+            title = full.title
+            emoji = full.emoji
+            text = full.text
+            collectionId = full.collectionId
+            isFullWidth = full.fullWidth ?? false
+        } catch {
+            errorMessage = "Couldn't load this document. Check your connection and try again."
+        }
+
+        children = (try? await apiClient.listDocuments(
+            collectionId: nil,
+            parentDocumentId: documentId,
+            offset: 0,
+            limit: 100
+        )) ?? []
+    }
+
+    func loadViewers() async {
+        guard let views = try? await apiClient.listViews(ListViewsRequest(documentId: documentId)) else { return }
+        viewers = views.filter { $0.lastViewedAt != nil }
+    }
+
+    func loadPinAndSubscriptionState() async {
+        if let pins = try? await apiClient.listPins(ListPinsRequest(collectionId: collectionId)),
+           let match = pins.first(where: { $0.documentId == documentId }) {
+            isPinned = true
+            pinId = match.id
+        } else {
+            isPinned = false
+            pinId = nil
+        }
+
+        if let subscriptions = try? await apiClient.listSubscriptions(ListSubscriptionsRequest(documentId: documentId)),
+           let match = subscriptions.first {
+            isSubscribed = true
+            subscriptionId = match.id
+        } else {
+            isSubscribed = false
+            subscriptionId = nil
+        }
+    }
+
+    func loadShare() async {
+        share = try? await apiClient.shareInfo(documentId: documentId)
+    }
+
+    func togglePin() async throws {
+        if let pinId {
+            self.pinId = nil
+            isPinned = false
+            do {
+                try await apiClient.deletePin(id: pinId)
+            } catch {
+                self.pinId = pinId
+                isPinned = true
+                throw error
+            }
+        } else {
+            let pin = try await apiClient.createPin(CreatePinRequest(documentId: documentId, collectionId: collectionId))
+            pinId = pin.id
+            isPinned = true
+        }
+    }
+
+    func toggleSubscription() async throws {
+        if let subscriptionId {
+            self.subscriptionId = nil
+            isSubscribed = false
+            do {
+                try await apiClient.deleteSubscription(id: subscriptionId)
+            } catch {
+                self.subscriptionId = subscriptionId
+                isSubscribed = true
+                throw error
+            }
+        } else {
+            let subscription = try await apiClient.createSubscription(CreateSubscriptionRequest(documentId: documentId))
+            subscriptionId = subscription.id
+            isSubscribed = true
+        }
+    }
+
+    func createOrLoadShare() async throws {
+        share = try await apiClient.createShare(CreateShareRequest(documentId: documentId))
+    }
+
+    /// Turning editing off saves; turning it on is just a mode switch.
+    func toggleEditing() async {
+        guard isEditing else {
+            isEditing = true
+            return
+        }
+        isSaving = true
+        saveErrorMessage = nil
+        defer { isSaving = false }
+        do {
+            let updated = try await apiClient.updateDocument(UpdateDocumentRequest(id: documentId, title: title, text: text))
+            title = updated.title
+            text = updated.text
+            isEditing = false
+        } catch {
+            saveErrorMessage = outlineErrorMessage(error, fallback: "Couldn't save this document.")
+        }
+    }
+
+    func toggleFullWidth() async throws {
+        let newValue = !isFullWidth
+        isFullWidth = newValue
+        do {
+            _ = try await apiClient.updateDocument(UpdateDocumentRequest(id: documentId, fullWidth: newValue))
+        } catch {
+            isFullWidth = !newValue
+            throw error
+        }
+    }
+
+    /// Fire-and-forget: `insightsEnabled` isn't readable back off `Document`
+    /// in the vendored spec, so there's no state to reflect as a checkmark.
+    func enableViewerInsights() async throws {
+        _ = try await apiClient.updateDocument(UpdateDocumentRequest(id: documentId, insightsEnabled: true))
+    }
+
+    /// Fire-and-forget, speculative field — see `UpdateDocumentRequest.documentEmbeds`.
+    func enableEmbeds() async throws {
+        _ = try await apiClient.updateDocument(UpdateDocumentRequest(id: documentId, documentEmbeds: true))
+    }
+}
diff --git a/Outpost/Features/Collections/DocumentRowView.swift b/Outpost/Features/Collections/DocumentRowView.swift
new file mode 100644
index 0000000..4164307
--- /dev/null
+++ b/Outpost/Features/Collections/DocumentRowView.swift
@@ -0,0 +1,30 @@
+import SwiftUI
+import OutlineKit
+
+struct DocumentRowView: View {
+    @Environment(StarStore.self) private var starStore
+
+    let document: OutlineDocument
+
+    var body: some View {
+        VStack(alignment: .leading, spacing: 2) {
+            HStack(spacing: 6) {
+                if let emoji = document.emoji {
+                    Text(emoji)
+                }
+                Text(document.title.isEmpty ? "Untitled" : document.title)
+                    .font(.body)
+                    .lineLimit(1)
+
+                if starStore.isStarred(documentId: document.id) {
+                    Image(systemName: "star.fill")
+                        .font(.caption2)
+                        .foregroundStyle(.yellow)
+                }
+            }
+            Text(document.updatedAt, format: .relative(presentation: .named))
+                .font(.caption)
+                .foregroundStyle(.secondary)
+        }
+    }
+}
diff --git a/Outpost/Features/Collections/DocumentSearchSheet.swift b/Outpost/Features/Collections/DocumentSearchSheet.swift
new file mode 100644
index 0000000..849e8cc
--- /dev/null
+++ b/Outpost/Features/Collections/DocumentSearchSheet.swift
@@ -0,0 +1,145 @@
+#if os(macOS)
+import SwiftUI
+import OutlineKit
+
+/// In-document find. `MarkdownEngine`'s `NativeTextViewWrapper` doesn't expose
+/// its underlying `NSTextView` (no `NSTextFinder`/coordinator access in its
+/// public API), so this renders the raw markdown source as plain per-line
+/// text instead of the styled reader view — the tradeoff is losing rich
+/// rendering in exchange for real match highlighting and scroll-to-match via
+/// `ScrollViewReader`, which wouldn't be possible against an opaque view.
+@MainActor
+struct DocumentSearchSheet: View {
+    @Environment(\.dismiss) private var dismiss
+
+    let apiClient: OutlineAPIClient
+    let document: OutlineDocument
+
+    @State private var lines: [String] = []
+    @State private var isLoading = false
+    @State private var errorMessage: String?
+    @State private var query = ""
+    @State private var currentMatchIndex = 0
+    @FocusState private var isSearchFieldFocused: Bool
+
+    private var matchingLineIndices: [Int] {
+        guard !query.isEmpty else { return [] }
+        return lines.indices.filter { lines[$0].localizedCaseInsensitiveContains(query) }
+    }
+
+    var body: some View {
+        VStack(spacing: 0) {
+            HStack {
+                Image(systemName: "magnifyingglass")
+                    .foregroundStyle(.secondary)
+                TextField("Search in \"\(document.title.isEmpty ? "Untitled" : document.title)\"", text: $query)
+                    .textFieldStyle(.plain)
+                    .focused($isSearchFieldFocused)
+                    .onChange(of: query) { currentMatchIndex = 0 }
+
+                if !matchingLineIndices.isEmpty {
+                    Text("\(currentMatchIndex + 1) of \(matchingLineIndices.count)")
+                        .font(.caption)
+                        .foregroundStyle(.secondary)
+                    Button {
+                        step(-1)
+                    } label: {
+                        Image(systemName: "chevron.up")
+                    }
+                    Button {
+                        step(1)
+                    } label: {
+                        Image(systemName: "chevron.down")
+                    }
+                } else if !query.isEmpty {
+                    Text("No matches")
+                        .font(.caption)
+                        .foregroundStyle(.secondary)
+                }
+
+                Button("Done") { dismiss() }
+            }
+            .padding()
+
+            Divider()
+
+            Group {
+                if isLoading && lines.isEmpty {
+                    ProgressView().frame(maxWidth: .infinity, maxHeight: .infinity)
+                } else if let errorMessage {
+                    ContentUnavailableView {
+                        Label("Couldn't Load Document", systemImage: "exclamationmark.triangle")
+                    } description: {
+                        Text(errorMessage)
+                    }
+                } else {
+                    ScrollViewReader { proxy in
+                        ScrollView {
+                            LazyVStack(alignment: .leading, spacing: 4) {
+                                ForEach(Array(lines.enumerated()), id: \.offset) { index, line in
+                                    Text(line.isEmpty ? " " : line)
+                                        .font(.system(.body, design: .monospaced))
+                                        .frame(maxWidth: .infinity, alignment: .leading)
+                                        .padding(.horizontal, 4)
+                                        .background(
+                                            isCurrentMatch(index) ? Color.yellow.opacity(0.4)
+                                                : matchingLineIndices.contains(index) ? Color.yellow.opacity(0.15)
+                                                : Color.clear
+                                        )
+                                        .id(index)
+                                }
+                            }
+                            .padding()
+                        }
+                        .onChange(of: currentMatchIndex) {
+                            guard let target = matchingLineIndices[safe: currentMatchIndex] else { return }
+                            withAnimation {
+                                proxy.scrollTo(target, anchor: .center)
+                            }
+                        }
+                        .onChange(of: query) {
+                            guard let target = matchingLineIndices.first else { return }
+                            withAnimation {
+                                proxy.scrollTo(target, anchor: .center)
+                            }
+                        }
+                    }
+                }
+            }
+            .frame(maxWidth: .infinity, maxHeight: .infinity)
+        }
+        .frame(width: 640, height: 520)
+        .task {
+            await load()
+            isSearchFieldFocused = true
+        }
+    }
+
+    private func isCurrentMatch(_ index: Int) -> Bool {
+        matchingLineIndices[safe: currentMatchIndex] == index
+    }
+
+    private func step(_ delta: Int) {
+        guard !matchingLineIndices.isEmpty else { return }
+        let count = matchingLineIndices.count
+        currentMatchIndex = ((currentMatchIndex + delta) % count + count) % count
+    }
+
+    private func load() async {
+        isLoading = true
+        defer { isLoading = false }
+        do {
+            let text = try await apiClient.documentInfo(id: document.id).text
+            lines = text.components(separatedBy: "\n")
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Couldn't load this document.")
+        }
+    }
+}
+
+private extension Array {
+    subscript(safe index: Int) -> Element? {
+        indices.contains(index) ? self[index] : nil
+    }
+}
+#endif
diff --git a/Outpost/Features/Collections/DocumentShareSheet.swift b/Outpost/Features/Collections/DocumentShareSheet.swift
new file mode 100644
index 0000000..1cae350
--- /dev/null
+++ b/Outpost/Features/Collections/DocumentShareSheet.swift
@@ -0,0 +1,112 @@
+#if os(macOS)
+import AppKit
+import SwiftUI
+import OutlineKit
+
+@MainActor
+struct DocumentShareSheet: View {
+    @Environment(\.dismiss) private var dismiss
+
+    let apiClient: OutlineAPIClient
+    let documentId: String
+
+    @State private var share: OutlineShare?
+    @State private var isLoading = false
+    @State private var isUpdating = false
+    @State private var errorMessage: String?
+    @State private var didCopy = false
+
+    var body: some View {
+        VStack(alignment: .leading, spacing: 16) {
+            HStack {
+                Text("Share")
+                    .font(.headline)
+                Spacer()
+                Button("Done") { dismiss() }
+            }
+
+            if isLoading {
+                ProgressView().frame(maxWidth: .infinity)
+            } else if let errorMessage {
+                Text(errorMessage)
+                    .font(.callout)
+                    .foregroundStyle(.red)
+            } else if let share {
+                HStack {
+                    Text(share.url)
+                        .font(.callout)
+                        .lineLimit(1)
+                        .truncationMode(.middle)
+                    Spacer()
+                    Button {
+                        copyLink(share.url)
+                    } label: {
+                        Image(systemName: didCopy ? "checkmark" : "doc.on.doc")
+                    }
+                    .buttonStyle(.plain)
+                }
+                .padding(8)
+                .background(.fill.tertiary, in: RoundedRectangle(cornerRadius: 6))
+
+                Toggle(
+                    "Published — accessible without sign-in",
+                    isOn: Binding(
+                        get: { share.published },
+                        set: { newValue in Task { await setPublished(newValue) } }
+                    )
+                )
+                .disabled(isUpdating)
+            } else {
+                Button("Create Share Link") {
+                    Task { await create() }
+                }
+            }
+        }
+        .padding(20)
+        .frame(width: 380)
+        .task { await load() }
+    }
+
+    private func copyLink(_ url: String) {
+        let pasteboard = NSPasteboard.general
+        pasteboard.clearContents()
+        pasteboard.setString(url, forType: .string)
+        didCopy = true
+        Task {
+            try? await Task.sleep(for: .seconds(1.5))
+            didCopy = false
+        }
+    }
+
+    private func load() async {
+        isLoading = true
+        defer { isLoading = false }
+        do {
+            share = try await apiClient.shareInfo(documentId: documentId)
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Couldn't load sharing info.")
+        }
+    }
+
+    private func create() async {
+        isLoading = true
+        defer { isLoading = false }
+        do {
+            share = try await apiClient.createShare(CreateShareRequest(documentId: documentId))
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Couldn't create a share link.")
+        }
+    }
+
+    private func setPublished(_ published: Bool) async {
+        guard let share else { return }
+        isUpdating = true
+        defer { isUpdating = false }
+        do {
+            self.share = try await apiClient.updateShare(UpdateShareRequest(id: share.id, published: published))
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Couldn't update this share link.")
+        }
+    }
+}
+#endif
diff --git a/Outpost/Features/Collections/DocumentsPane.swift b/Outpost/Features/Collections/DocumentsPane.swift
new file mode 100644
index 0000000..7bc2b0e
--- /dev/null
+++ b/Outpost/Features/Collections/DocumentsPane.swift
@@ -0,0 +1,17 @@
+import SwiftUI
+import OutlineKit
+
+/// Holds `DocumentsViewModel` in `@State` so callers that construct this from a
+/// computed/closure context (`NavigationSplitView.detail`, `navigationDestination`)
+/// don't rebuild — and reset — it on every unrelated re-render.
+struct DocumentsPane: View {
+    @State private var viewModel: DocumentsViewModel
+
+    init(apiClient: OutlineAPIClient, collection: OutlineCollection) {
+        _viewModel = State(initialValue: DocumentsViewModel(apiClient: apiClient, collection: collection))
+    }
+
+    var body: some View {
+        DocumentListContent(viewModel: viewModel)
+    }
+}
diff --git a/Outpost/Features/Collections/DocumentsViewModel.swift b/Outpost/Features/Collections/DocumentsViewModel.swift
new file mode 100644
index 0000000..0c5181d
--- /dev/null
+++ b/Outpost/Features/Collections/DocumentsViewModel.swift
@@ -0,0 +1,50 @@
+import Foundation
+import Observation
+import OutlineKit
+
+@MainActor
+@Observable
+final class DocumentsViewModel {
+    private(set) var documents: [OutlineDocument] = []
+    var isLoading = false
+    var errorMessage: String?
+    var hasRemoteChanges = false
+
+    let collection: OutlineCollection
+    private let apiClient: OutlineAPIClient
+
+    init(apiClient: OutlineAPIClient, collection: OutlineCollection) {
+        self.apiClient = apiClient
+        self.collection = collection
+    }
+
+    func load() async {
+        isLoading = true
+        errorMessage = nil
+        defer { isLoading = false }
+
+        do {
+            documents = try await apiClient.listDocuments(collectionId: collection.id, parentDocumentId: nil, offset: 0, limit: 100)
+            hasRemoteChanges = false
+        } catch {
+            errorMessage = "Couldn't load documents. Check your connection and try again."
+        }
+    }
+
+    /// See CollectionsViewModel.checkForRemoteChanges — same reasoning.
+    func checkForRemoteChanges() async {
+        guard let fresh = try? await apiClient.listDocuments(collectionId: collection.id, parentDocumentId: nil, offset: 0, limit: 100) else {
+            return
+        }
+        if Self.fingerprint(fresh) != Self.fingerprint(documents) {
+            hasRemoteChanges = true
+        }
+    }
+
+    private static func fingerprint(_ documents: [OutlineDocument]) -> String {
+        documents
+            .map { "\($0.id):\($0.updatedAt.timeIntervalSince1970)" }
+            .sorted()
+            .joined(separator: "|")
+    }
+}
diff --git a/Outpost/Features/Collections/MoveDocumentSheet.swift b/Outpost/Features/Collections/MoveDocumentSheet.swift
new file mode 100644
index 0000000..996701f
--- /dev/null
+++ b/Outpost/Features/Collections/MoveDocumentSheet.swift
@@ -0,0 +1,123 @@
+#if os(macOS)
+import SwiftUI
+import OutlineKit
+
+/// Destination picker for `documents.move` — collection, then optionally a
+/// root-level document in that collection to nest under. Doesn't offer
+/// picking a destination deeper than one level (i.e. can't move under a
+/// grandchild) — kept intentionally shallow rather than mirroring the full
+/// sidebar tree in a picker.
+@MainActor
+struct MoveDocumentSheet: View {
+    @Environment(\.dismiss) private var dismiss
+
+    let apiClient: OutlineAPIClient
+    let document: OutlineDocument
+    let onMoved: () async -> Void
+
+    @State private var collections: [OutlineCollection] = []
+    @State private var selectedCollectionID: String?
+    @State private var rootDocuments: [OutlineDocument] = []
+    @State private var selectedParentID: String?
+    @State private var isLoadingCollections = false
+    @State private var isLoadingDestinationDocuments = false
+    @State private var isMoving = false
+    @State private var errorMessage: String?
+
+    var body: some View {
+        VStack(alignment: .leading, spacing: 16) {
+            Text("Move \"\(document.title.isEmpty ? "Untitled" : document.title)\"")
+                .font(.headline)
+
+            if isLoadingCollections {
+                ProgressView().frame(maxWidth: .infinity)
+            } else {
+                Picker("Collection", selection: $selectedCollectionID) {
+                    Text("Choose a collection").tag(String?.none)
+                    ForEach(collections) { collection in
+                        Text(collection.name).tag(Optional(collection.id))
+                    }
+                }
+                .labelsHidden()
+
+                Picker("Location", selection: $selectedParentID) {
+                    Text("Collection root").tag(String?.none)
+                    ForEach(rootDocuments.filter { $0.id != document.id }) { candidate in
+                        Text(candidate.title.isEmpty ? "Untitled" : candidate.title).tag(Optional(candidate.id))
+                    }
+                }
+                .labelsHidden()
+                .disabled(selectedCollectionID == nil || isLoadingDestinationDocuments)
+            }
+
+            if let errorMessage {
+                Text(errorMessage)
+                    .font(.callout)
+                    .foregroundStyle(.red)
+            }
+
+            HStack {
+                Spacer()
+                Button("Cancel", role: .cancel) { dismiss() }
+                Button("Move") {
+                    Task { await move() }
+                }
+                .disabled(selectedCollectionID == nil || isMoving)
+            }
+        }
+        .padding(20)
+        .frame(width: 360)
+        .task {
+            await loadCollections()
+            selectedCollectionID = document.collectionId
+        }
+        .task(id: selectedCollectionID) {
+            await loadRootDocuments()
+        }
+    }
+
+    private func loadCollections() async {
+        isLoadingCollections = true
+        defer { isLoadingCollections = false }
+        do {
+            collections = try await apiClient.listCollections(offset: 0, limit: 100)
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Couldn't load collections.")
+        }
+    }
+
+    private func loadRootDocuments() async {
+        guard let selectedCollectionID else {
+            rootDocuments = []
+            return
+        }
+        isLoadingDestinationDocuments = true
+        defer { isLoadingDestinationDocuments = false }
+        do {
+            rootDocuments = try await apiClient.listDocuments(
+                collectionId: selectedCollectionID,
+                parentDocumentId: nil,
+                offset: 0,
+                limit: 100
+            )
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Couldn't load destination documents.")
+        }
+    }
+
+    private func move() async {
+        guard let selectedCollectionID else { return }
+        isMoving = true
+        defer { isMoving = false }
+        do {
+            try await apiClient.moveDocument(
+                MoveDocumentRequest(id: document.id, collectionId: selectedCollectionID, parentDocumentId: selectedParentID)
+            )
+            await onMoved()
+            dismiss()
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Couldn't move this document.")
+        }
+    }
+}
+#endif
diff --git a/Outpost/Features/Collections/RemoteChangesBanner.swift b/Outpost/Features/Collections/RemoteChangesBanner.swift
new file mode 100644
index 0000000..4bd8046
--- /dev/null
+++ b/Outpost/Features/Collections/RemoteChangesBanner.swift
@@ -0,0 +1,26 @@
+#if os(macOS)
+import SwiftUI
+
+/// Shown when a periodic background check finds the server has changes we
+/// don't have — doesn't auto-refresh, since that would silently replace
+/// what's on screen (losing scroll position, expanded rows) without asking.
+struct RemoteChangesBanner: View {
+    let onRefresh: () -> Void
+
+    var body: some View {
+        HStack(spacing: 8) {
+            Image(systemName: "arrow.triangle.2.circlepath")
+                .foregroundStyle(Color.accentColor)
+            Text("New changes available")
+                .font(.callout)
+            Spacer(minLength: 8)
+            Button("Refresh", action: onRefresh)
+                .buttonStyle(.borderedProminent)
+                .controlSize(.small)
+        }
+        .padding(.horizontal, 12)
+        .padding(.vertical, 8)
+        .background(Color.accentColor.opacity(0.12))
+    }
+}
+#endif
diff --git a/Outpost/Features/Collections/SidebarSortOption.swift b/Outpost/Features/Collections/SidebarSortOption.swift
new file mode 100644
index 0000000..bd043ed
--- /dev/null
+++ b/Outpost/Features/Collections/SidebarSortOption.swift
@@ -0,0 +1,39 @@
+import Foundation
+import OutlineKit
+
+/// Ordering for the nested document outline under a sidebar collection.
+///
+/// Outline's `Collection.sort` field exists for this, but its own OpenAPI spec
+/// notes it's "left as a frontend concern to implement" and `collections.update`
+/// doesn't document a `sort` param to persist it — so this stays a local,
+/// per-session preference rather than a synced setting.
+enum SidebarSortOption: String, CaseIterable, Identifiable {
+    case manual
+    case alphabetical
+    case dateCreated
+    case dateUpdated
+
+    var id: String { rawValue }
+
+    var label: String {
+        switch self {
+        case .manual: return "Manual"
+        case .alphabetical: return "A–Z"
+        case .dateCreated: return "Date Created"
+        case .dateUpdated: return "Date Updated"
+        }
+    }
+
+    func sorted(_ documents: [OutlineDocument]) -> [OutlineDocument] {
+        switch self {
+        case .manual:
+            return documents
+        case .alphabetical:
+            return documents.sorted { $0.title.localizedStandardCompare($1.title) == .orderedAscending }
+        case .dateCreated:
+            return documents.sorted { $0.createdAt > $1.createdAt }
+        case .dateUpdated:
+            return documents.sorted { $0.updatedAt > $1.updatedAt }
+        }
+    }
+}
diff --git a/Outpost/Features/Search/DocumentTitleSearchViewModel.swift b/Outpost/Features/Search/DocumentTitleSearchViewModel.swift
new file mode 100644
index 0000000..15da66f
--- /dev/null
+++ b/Outpost/Features/Search/DocumentTitleSearchViewModel.swift
@@ -0,0 +1,48 @@
+import Foundation
+import Observation
+import OutlineKit
+
+/// Backs the contextual toolbar search — matches scoped to whichever collection
+/// is currently open ("search what you're looking at").
+///
+/// Uses `documents.search` rather than `documents.search_titles`: the latter
+/// consistently failed against the connected server (likely unavailable on
+/// this Outline version — see ARCHITECTURE.md's note on server version drift),
+/// while `documents.search` is the same, longer-established endpoint the
+/// sidebar's global search already relies on.
+@MainActor
+@Observable
+final class DocumentTitleSearchViewModel {
+    var results: [OutlineDocumentSearchResult] = []
+    var isSearching = false
+    var errorMessage: String?
+
+    private let apiClient: OutlineAPIClient
+    private let collectionId: String
+
+    init(apiClient: OutlineAPIClient, collectionId: String) {
+        self.apiClient = apiClient
+        self.collectionId = collectionId
+    }
+
+    func search(query: String) async {
+        let trimmed = query.trimmingCharacters(in: .whitespacesAndNewlines)
+        guard !trimmed.isEmpty else {
+            results = []
+            errorMessage = nil
+            return
+        }
+
+        isSearching = true
+        errorMessage = nil
+        defer { isSearching = false }
+
+        do {
+            results = try await apiClient.searchDocuments(
+                DocumentSearchRequest(query: trimmed, collectionId: collectionId)
+            )
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Search failed. Try again.")
+        }
+    }
+}
diff --git a/Outpost/Features/Search/GlobalSearchResultsView.swift b/Outpost/Features/Search/GlobalSearchResultsView.swift
new file mode 100644
index 0000000..5780e4e
--- /dev/null
+++ b/Outpost/Features/Search/GlobalSearchResultsView.swift
@@ -0,0 +1,141 @@
+#if os(macOS)
+import SwiftUI
+import OutlineKit
+
+struct GlobalSearchResultsView: View {
+    @State private var viewModel: GlobalSearchViewModel
+    let query: String
+    let onOpenDocument: (OutlineDocument) -> Void
+
+    init(apiClient: OutlineAPIClient, query: String, onOpenDocument: @escaping (OutlineDocument) -> Void) {
+        _viewModel = State(initialValue: GlobalSearchViewModel(apiClient: apiClient))
+        self.query = query
+        self.onOpenDocument = onOpenDocument
+    }
+
+    private var searchKey: String {
+        [
+            query,
+            viewModel.collectionFilter?.id ?? "",
+            viewModel.dateFilter?.rawValue ?? "",
+            viewModel.sort.rawValue,
+            viewModel.direction.rawValue,
+            viewModel.statusFilter.map(\.rawValue).sorted().joined(separator: ",")
+        ].joined(separator: "|")
+    }
+
+    var body: some View {
+        // No `.navigationTitle` — `ContentView_macOS`'s leading toolbar item
+        // already shows a "Search" pill while global search is active.
+        results
+            .toolbar {
+                ToolbarItemGroup(placement: .primaryAction) {
+                    collectionPicker
+                    sortPicker
+                    dateFilterPicker
+                    statusFilterMenu
+                }
+            }
+            .task { await viewModel.loadCollectionsIfNeeded() }
+            .task(id: searchKey) {
+                try? await Task.sleep(for: .milliseconds(300))
+                guard !Task.isCancelled else { return }
+                await viewModel.search(query: query)
+            }
+    }
+
+    // `documents.search`'s `collectionId` is a single UUID, not an array — this
+    // stays single-select because that's genuinely all the endpoint supports,
+    // not an arbitrary UI limitation.
+    private var collectionPicker: some View {
+        Picker("Collection", selection: $viewModel.collectionFilter) {
+            Text("All Collections").tag(OutlineCollection?.none)
+            ForEach(viewModel.availableCollections) { collection in
+                Text(collection.name).tag(Optional(collection))
+            }
+        }
+        .padding(.horizontal, 4)
+    }
+
+    private var sortPicker: some View {
+        Picker("Sort", selection: $viewModel.sort) {
+            Text("Relevance").tag(DocumentSearchSort.relevance)
+            Text("Updated").tag(DocumentSearchSort.updatedAt)
+            Text("Created").tag(DocumentSearchSort.createdAt)
+            Text("Title").tag(DocumentSearchSort.title)
+        }
+        .padding(.horizontal, 4)
+    }
+
+    private var dateFilterPicker: some View {
+        Picker("Date", selection: $viewModel.dateFilter) {
+            Text("Any Time").tag(DocumentSearchDateFilter?.none)
+            Text("Past Day").tag(Optional(DocumentSearchDateFilter.day))
+            Text("Past Week").tag(Optional(DocumentSearchDateFilter.week))
+            Text("Past Month").tag(Optional(DocumentSearchDateFilter.month))
+            Text("Past Year").tag(Optional(DocumentSearchDateFilter.year))
+        }
+        .padding(.horizontal, 4)
+    }
+
+    private var statusFilterMenu: some View {
+        Menu {
+            ForEach(DocumentStatusFilter.allCases, id: \.self) { status in
+                Button {
+                    if viewModel.statusFilter.contains(status) {
+                        viewModel.statusFilter.remove(status)
+                    } else {
+                        viewModel.statusFilter.insert(status)
+                    }
+                } label: {
+                    // `Label(_:systemImage:)` with an empty string logs "No
+                    // symbol named ''" — use the icon-closure init instead so
+                    // the unselected case can render no icon at all.
+                    Label {
+                        Text(status.rawValue.capitalized)
+                    } icon: {
+                        if viewModel.statusFilter.contains(status) {
+                            Image(systemName: "checkmark")
+                        }
+                    }
+                }
+            }
+        } label: {
+            Text(viewModel.statusFilter.isEmpty ? "Any Status" : "\(viewModel.statusFilter.count) Status")
+        }
+        .padding(.horizontal, 4)
+    }
+
+    @ViewBuilder
+    private var results: some View {
+        if viewModel.isSearching && viewModel.results.isEmpty {
+            ProgressView()
+                .frame(maxWidth: .infinity, maxHeight: .infinity)
+        } else if let errorMessage = viewModel.errorMessage {
+            ContentUnavailableView {
+                Label("Search Failed", systemImage: "exclamationmark.triangle")
+            } description: {
+                Text(errorMessage)
+            }
+        } else if viewModel.results.isEmpty {
+            ContentUnavailableView.search(text: query)
+        } else {
+            List(viewModel.results) { result in
+                Button {
+                    onOpenDocument(result.document)
+                } label: {
+                    VStack(alignment: .leading, spacing: 4) {
+                        DocumentRowView(document: result.document)
+                        Text(result.context)
+                            .font(.callout)
+                            .foregroundStyle(.secondary)
+                            .lineLimit(2)
+                    }
+                    .padding(.vertical, 2)
+                }
+                .buttonStyle(.plain)
+            }
+        }
+    }
+}
+#endif
diff --git a/Outpost/Features/Search/GlobalSearchViewModel.swift b/Outpost/Features/Search/GlobalSearchViewModel.swift
new file mode 100644
index 0000000..a97324e
--- /dev/null
+++ b/Outpost/Features/Search/GlobalSearchViewModel.swift
@@ -0,0 +1,62 @@
+import Foundation
+import Observation
+import OutlineKit
+
+/// Backs the sidebar's whole-workspace search — full-text via `documents.search`,
+/// with filters mirroring what that endpoint actually supports.
+@MainActor
+@Observable
+final class GlobalSearchViewModel {
+    var results: [OutlineDocumentSearchResult] = []
+    var availableCollections: [OutlineCollection] = []
+    var isSearching = false
+    var errorMessage: String?
+
+    var collectionFilter: OutlineCollection?
+    var dateFilter: DocumentSearchDateFilter?
+    var sort: DocumentSearchSort = .relevance
+    var direction: DocumentSearchDirection = .descending
+    var statusFilter: Set<DocumentStatusFilter> = []
+
+    private let apiClient: OutlineAPIClient
+
+    init(apiClient: OutlineAPIClient) {
+        self.apiClient = apiClient
+    }
+
+    func loadCollectionsIfNeeded() async {
+        guard availableCollections.isEmpty else { return }
+        availableCollections = (try? await apiClient.listCollections(offset: 0, limit: 100)) ?? []
+    }
+
+    func search(query: String) async {
+        let trimmed = query.trimmingCharacters(in: .whitespacesAndNewlines)
+        guard !trimmed.isEmpty else {
+            results = []
+            errorMessage = nil
+            return
+        }
+
+        isSearching = true
+        errorMessage = nil
+        defer { isSearching = false }
+
+        do {
+            results = try await apiClient.searchDocuments(
+                DocumentSearchRequest(
+                    query: trimmed,
+                    collectionId: collectionFilter?.id,
+                    statusFilter: statusFilter.isEmpty ? nil : Array(statusFilter),
+                    dateFilter: dateFilter,
+                    // The server rejects `sort: "relevance"` outright — it's
+                    // apparently only valid as the *implicit* default when the
+                    // field is omitted entirely, not as an explicit value.
+                    sort: sort == .relevance ? nil : sort,
+                    direction: direction
+                )
+            )
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Search failed. Try again.")
+        }
+    }
+}
diff --git a/Outpost/Features/Search/SidebarSearchField.swift b/Outpost/Features/Search/SidebarSearchField.swift
new file mode 100644
index 0000000..213867f
--- /dev/null
+++ b/Outpost/Features/Search/SidebarSearchField.swift
@@ -0,0 +1,30 @@
+#if os(macOS)
+import SwiftUI
+
+struct SidebarSearchField: View {
+    @Binding var text: String
+
+    var body: some View {
+        HStack(spacing: 6) {
+            Image(systemName: "magnifyingglass")
+                .foregroundStyle(.secondary)
+            TextField("Search workspace…", text: $text)
+                .textFieldStyle(.plain)
+            if !text.isEmpty {
+                Button {
+                    text = ""
+                } label: {
+                    Image(systemName: "xmark.circle.fill")
+                        .foregroundStyle(.secondary)
+                }
+                .buttonStyle(.plain)
+            }
+        }
+        .padding(.horizontal, 10)
+        .padding(.vertical, 6)
+        .background(.fill.tertiary, in: RoundedRectangle(cornerRadius: 8))
+        .padding(.horizontal, 10)
+        .padding(.vertical, 8)
+    }
+}
+#endif
diff --git a/Outpost/Item.swift b/Outpost/Item.swift
deleted file mode 100644
index 344e52f..0000000
--- a/Outpost/Item.swift
+++ /dev/null
@@ -1,18 +0,0 @@
-//
-//  Item.swift
-//  Outpost
-//
-//  Created by Puranjay Savar Mattas on 12/08/26.
-//
-
-import Foundation
-import SwiftData
-
-@Model
-final class Item {
-    var timestamp: Date
-    
-    init(timestamp: Date) {
-        self.timestamp = timestamp
-    }
-}
diff --git a/Outpost/Outpost.entitlements b/Outpost/Outpost.entitlements
new file mode 100644
index 0000000..ee95ab7
--- /dev/null
+++ b/Outpost/Outpost.entitlements
@@ -0,0 +1,10 @@
+<?xml version="1.0" encoding="UTF-8"?>
+<!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
+<plist version="1.0">
+<dict>
+	<key>com.apple.security.app-sandbox</key>
+	<true/>
+	<key>com.apple.security.network.client</key>
+	<true/>
+</dict>
+</plist>
diff --git a/Outpost/OutpostApp.swift b/Outpost/OutpostApp.swift
index ab99140..49caa0c 100644
--- a/Outpost/OutpostApp.swift
+++ b/Outpost/OutpostApp.swift
@@ -6,27 +6,85 @@
 //
 
 import SwiftUI
-import SwiftData
+
+#if os(macOS)
+import AppKit
+#endif
 
 @main
 struct OutpostApp: App {
-    var sharedModelContainer: ModelContainer = {
-        let schema = Schema([
-            Item.self,
-        ])
-        let modelConfiguration = ModelConfiguration(schema: schema, isStoredInMemoryOnly: false)
+    @State private var session = SessionStore()
+    @AppStorage("outpost.appearance") private var appearance: AppAppearance = .system
 
-        do {
-            return try ModelContainer(for: schema, configurations: [modelConfiguration])
-        } catch {
-            fatalError("Could not create ModelContainer: \(error)")
-        }
-    }()
+    #if os(macOS)
+    @Environment(\.openWindow) private var openWindow
+    @State private var isShowingLogoutConfirmation = false
+    #endif
 
     var body: some Scene {
         WindowGroup {
-            ContentView()
+            RootView()
+                .environment(session)
+                #if os(iOS)
+                .preferredColorScheme(appearance.colorScheme)
+                #endif
+                #if os(macOS)
+                .onAppear { applyMacAppearance() }
+                .onChange(of: appearance) { _, _ in applyMacAppearance() }
+                .logoutConfirmationDialog(isPresented: $isShowingLogoutConfirmation, session: session)
+                #endif
         }
-        .modelContainer(sharedModelContainer)
+        #if os(macOS)
+        .commands {
+            CommandGroup(replacing: .appInfo) {
+                Button("About Outpost") {
+                    openWindow(id: "about")
+                }
+            }
+            CommandGroup(after: .appSettings) {
+                Divider()
+                Button("Log Out…") {
+                    isShowingLogoutConfirmation = true
+                }
+                .disabled(!session.isSignedIn)
+            }
+        }
+        #endif
+
+        #if os(macOS)
+        Window("About Outpost", id: "about") {
+            AboutView()
+                .disablesFullScreen()
+        }
+        .windowResizability(.contentSize)
+
+        Window("Keyboard Shortcuts", id: "keyboard-shortcuts") {
+            KeyboardShortcutsView()
+                .disablesFullScreen()
+        }
+        .windowResizability(.contentSize)
+
+        Settings {
+            PreferencesView()
+                .environment(session)
+        }
+        #endif
     }
+
+    #if os(macOS)
+    /// `.preferredColorScheme(nil)` doesn't reliably reset the window's real
+    /// `NSAppearance` back to "follow system" after an explicit override — this
+    /// sets the actual AppKit-level appearance directly instead, which every
+    /// window (present and future) inherits.
+    private func applyMacAppearance() {
+        switch appearance {
+        case .system:
+            NSApp.appearance = nil
+        case .light:
+            NSApp.appearance = NSAppearance(named: .aqua)
+        case .dark:
+            NSApp.appearance = NSAppearance(named: .darkAqua)
+        }
+    }
+    #endif
 }
diff --git a/Outpost/Root/RootView.swift b/Outpost/Root/RootView.swift
new file mode 100644
index 0000000..5b25277
--- /dev/null
+++ b/Outpost/Root/RootView.swift
@@ -0,0 +1,48 @@
+import SwiftUI
+import OutlineKit
+
+struct RootView: View {
+    @Environment(SessionStore.self) private var session
+    @State private var welcomeName: String?
+    @State private var starStore = StarStore()
+
+    var body: some View {
+        ZStack {
+            if session.isSignedIn {
+                ContentView()
+            } else {
+                AuthView(onSigningIn: startWelcomeTransition)
+            }
+
+            if let welcomeName {
+                WelcomeSplashView(name: welcomeName)
+                    .transition(.opacity)
+                    .zIndex(1)
+            }
+        }
+        .environment(starStore)
+        .animation(.easeInOut(duration: 0.45), value: welcomeName != nil)
+        .task {
+            await session.refreshTeamInfoIfNeeded()
+        }
+        .task(id: session.isSignedIn) {
+            if session.isSignedIn, let apiClient = session.apiClient {
+                await starStore.load(apiClient: apiClient)
+            } else {
+                starStore.reset()
+            }
+        }
+    }
+
+    private func startWelcomeTransition(_ result: AuthViewModel.AuthResult) {
+        welcomeName = result.user.name
+        session.signIn(serverURL: result.serverURL, user: result.user, team: result.team)
+
+        Task {
+            try? await Task.sleep(for: .seconds(1.1))
+            withAnimation(.easeInOut(duration: 0.45)) {
+                welcomeName = nil
+            }
+        }
+    }
+}
diff --git a/Outpost/Root/SessionStore.swift b/Outpost/Root/SessionStore.swift
new file mode 100644
index 0000000..d8563fe
--- /dev/null
+++ b/Outpost/Root/SessionStore.swift
@@ -0,0 +1,78 @@
+import Foundation
+import Observation
+import OutlineKit
+
+@MainActor
+@Observable
+final class SessionStore {
+    private static let serverURLDefaultsKey = "outline.serverURL"
+
+    private let tokenStore: TokenStoring
+    private let defaults: UserDefaults
+
+    var isSignedIn: Bool
+    var userName: String?
+    var userEmail: String?
+    var userAvatarURL: URL?
+    var teamName: String?
+    var teamAvatarURL: URL?
+    private(set) var apiClient: OutlineAPIClient?
+
+    var serverURL: URL? {
+        defaults.string(forKey: Self.serverURLDefaultsKey).flatMap(URL.init(string:))
+    }
+
+    init(tokenStore: TokenStoring = KeychainTokenStore(), defaults: UserDefaults = .standard) {
+        self.tokenStore = tokenStore
+        self.defaults = defaults
+        self.isSignedIn = (try? tokenStore.token()) != nil
+
+        if isSignedIn, let serverURL {
+            apiClient = LiveOutlineAPIClient(
+                configuration: OutlineConfiguration(baseURL: serverURL),
+                tokenStore: tokenStore
+            )
+        }
+    }
+
+    func signIn(serverURL: URL, user: OutlineUser, team: OutlineTeam) {
+        defaults.set(serverURL.absoluteString, forKey: Self.serverURLDefaultsKey)
+        apiClient = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: serverURL),
+            tokenStore: tokenStore
+        )
+        apply(user: user, team: team, serverURL: serverURL)
+        isSignedIn = true
+    }
+
+    func signOut() {
+        try? tokenStore.clear()
+        defaults.removeObject(forKey: Self.serverURLDefaultsKey)
+        isSignedIn = false
+        userName = nil
+        userEmail = nil
+        userAvatarURL = nil
+        teamName = nil
+        teamAvatarURL = nil
+        apiClient = nil
+    }
+
+    /// Re-fetches user/workspace name/logo on relaunch, when the token survived but this
+    /// in-memory state didn't.
+    func refreshTeamInfoIfNeeded() async {
+        guard isSignedIn, teamName == nil, let apiClient, let serverURL else { return }
+        guard let auth = try? await apiClient.authInfo() else { return }
+        apply(user: auth.user, team: auth.team, serverURL: serverURL)
+    }
+
+    private func apply(user: OutlineUser, team: OutlineTeam, serverURL: URL) {
+        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 }
+        teamName = team.name
+        teamAvatarURL = team.avatarUrl.flatMap { URL(string: $0, relativeTo: serverURL)?.absoluteURL }
+    }
+}
diff --git a/Outpost/Root/WelcomeSplashView.swift b/Outpost/Root/WelcomeSplashView.swift
new file mode 100644
index 0000000..c00203b
--- /dev/null
+++ b/Outpost/Root/WelcomeSplashView.swift
@@ -0,0 +1,41 @@
+import SwiftUI
+
+/// Full-window cover shown between a successful sign-in and `RootView` revealing the
+/// signed-in content beneath it, so the login form never has to visibly tear down.
+struct WelcomeSplashView: View {
+    let name: String
+
+    var body: some View {
+        ZStack {
+            Rectangle()
+                .fill(.background)
+                .ignoresSafeArea()
+
+            VStack(spacing: 20) {
+                ZStack {
+                    Circle()
+                        .fill(
+                            LinearGradient(
+                                colors: [Color.accentColor, Color.accentColor.opacity(0.6)],
+                                startPoint: .topLeading,
+                                endPoint: .bottomTrailing
+                            )
+                        )
+                        .frame(width: 88, height: 88)
+                    Image(systemName: "checkmark")
+                        .font(.system(size: 36, weight: .bold))
+                        .foregroundStyle(.white)
+                }
+                .shadow(color: Color.accentColor.opacity(0.35), radius: 16, y: 8)
+
+                VStack(spacing: 6) {
+                    Text("Welcome, \(name)")
+                        .font(.title2.bold())
+                    Text("Signing you in…")
+                        .font(.subheadline)
+                        .foregroundStyle(.secondary)
+                }
+            }
+        }
+    }
+}
diff --git a/Outpost/Support/AppAppearance.swift b/Outpost/Support/AppAppearance.swift
new file mode 100644
index 0000000..2405e97
--- /dev/null
+++ b/Outpost/Support/AppAppearance.swift
@@ -0,0 +1,23 @@
+import SwiftUI
+
+enum AppAppearance: String, CaseIterable, Identifiable {
+    case system, light, dark
+
+    var id: String { rawValue }
+
+    var label: String {
+        switch self {
+        case .system: return "System"
+        case .light: return "Light"
+        case .dark: return "Dark"
+        }
+    }
+
+    var colorScheme: ColorScheme? {
+        switch self {
+        case .system: return nil
+        case .light: return .light
+        case .dark: return .dark
+        }
+    }
+}
diff --git a/Outpost/Support/AvatarBadge.swift b/Outpost/Support/AvatarBadge.swift
new file mode 100644
index 0000000..bf35d89
--- /dev/null
+++ b/Outpost/Support/AvatarBadge.swift
@@ -0,0 +1,62 @@
+import SwiftUI
+
+#if os(macOS)
+import AppKit
+typealias PlatformImage = NSImage
+#else
+import UIKit
+typealias PlatformImage = UIImage
+#endif
+
+/// Loads the avatar manually instead of using `AsyncImage`, and flattens the result
+/// with `.drawingGroup()`. Hosted inside AppKit-backed controls (a macOS toolbar
+/// item, a `Menu` label), this content was observed blowing past its `.frame`/
+/// `.clipShape` constraints once the host re-measured it after the image loaded —
+/// `.drawingGroup()` rasterizes it to a fixed bitmap at the constrained size first,
+/// so there's nothing left for the host to re-measure.
+struct AvatarBadge: View {
+    let avatarURL: URL?
+    var size: CGFloat = 22
+    var placeholderSystemImage: String = "person.crop.circle.fill"
+
+    @State private var loadedImage: PlatformImage?
+
+    var body: some View {
+        ZStack {
+            Circle()
+                .fill(Color.accentColor.opacity(0.2))
+
+            if let loadedImage {
+                platformImage(loadedImage)
+                    .resizable()
+                    .scaledToFill()
+            } else {
+                placeholderIcon
+            }
+        }
+        .frame(width: size, height: size)
+        .clipShape(Circle())
+        .compositingGroup()
+        .drawingGroup()
+        .task(id: avatarURL) {
+            loadedImage = nil
+            guard let avatarURL else { return }
+            guard let (data, _) = try? await URLSession.shared.data(from: avatarURL) else { return }
+            loadedImage = PlatformImage(data: data)
+        }
+    }
+
+    private func platformImage(_ image: PlatformImage) -> Image {
+        #if os(macOS)
+        Image(nsImage: image)
+        #else
+        Image(uiImage: image)
+        #endif
+    }
+
+    private var placeholderIcon: some View {
+        Image(systemName: placeholderSystemImage)
+            .font(.system(size: size * 0.5, weight: .semibold))
+            .foregroundStyle(Color.accentColor)
+    }
+}
diff --git a/Outpost/Support/Color+Hex.swift b/Outpost/Support/Color+Hex.swift
new file mode 100644
index 0000000..be81b49
--- /dev/null
+++ b/Outpost/Support/Color+Hex.swift
@@ -0,0 +1,14 @@
+import SwiftUI
+
+extension Color {
+    init?(hex: String) {
+        var sanitized = hex.trimmingCharacters(in: .whitespacesAndNewlines)
+        sanitized.removeAll { $0 == "#" }
+        guard sanitized.count == 6, let value = UInt32(sanitized, radix: 16) else { return nil }
+        self.init(
+            red: Double((value >> 16) & 0xFF) / 255,
+            green: Double((value >> 8) & 0xFF) / 255,
+            blue: Double(value & 0xFF) / 255
+        )
+    }
+}
diff --git a/Outpost/Support/OutlineAPIError+Message.swift b/Outpost/Support/OutlineAPIError+Message.swift
new file mode 100644
index 0000000..012960f
--- /dev/null
+++ b/Outpost/Support/OutlineAPIError+Message.swift
@@ -0,0 +1,29 @@
+import Foundation
+import OutlineKit
+
+extension OutlineAPIError {
+    /// User-facing message, distinguishing failure causes instead of one blanket
+    /// "try again" — a 404 (e.g. an endpoint missing on an older server version)
+    /// looks nothing like a dropped connection, and surfacing that difference is
+    /// what actually helps diagnose it.
+    var userFacingMessage: String {
+        switch self {
+        case .unauthorized:
+            return "Sign-in expired. Try signing in again."
+        case .notFound:
+            return "That isn't available on this server."
+        case .transport:
+            return "Couldn't reach the server. Check your connection."
+        case .server(let status, let message):
+            return message ?? "The server returned an error (\(status))."
+        case .decoding:
+            return "Got an unexpected response from the server."
+        case .tokenUnavailable:
+            return "Couldn't access your saved sign-in."
+        }
+    }
+}
+
+func outlineErrorMessage(_ error: Error, fallback: String) -> String {
+    (error as? OutlineAPIError)?.userFacingMessage ?? fallback
+}
diff --git a/Outpost/Support/OutlineIconMapping.swift b/Outpost/Support/OutlineIconMapping.swift
new file mode 100644
index 0000000..41ec8c5
--- /dev/null
+++ b/Outpost/Support/OutlineIconMapping.swift
@@ -0,0 +1,96 @@
+import Foundation
+
+/// Best-effort SF Symbol equivalents for Outline's non-emoji collection icons.
+///
+/// `Collection.icon` is either a literal emoji or a string key into Outline's
+/// own icon set — a mix of custom `outline-icons` components (camelCase keys)
+/// and FontAwesome icons (kebab-case keys, e.g. `faCake` → `"cake"`). The
+/// canonical key list lives in `outline/outline`'s `shared/utils/IconLibrary.tsx`,
+/// not in the `outline-icons` package itself (that's just the raw component
+/// library, keyed by PascalCase component name — a different naming scheme).
+///
+/// SF Symbols has no exact match for everything in that set, so this only
+/// covers keys with a confident, unambiguous equivalent. Anything else falls
+/// back to the generic folder glyph — better than a blank/invalid symbol name
+/// from a wrong guess.
+enum OutlineIconMapping {
+    static func sfSymbolName(for outlineIconKey: String) -> String? {
+        mapping[outlineIconKey]
+    }
+
+    private static let mapping: [String: String] = [
+        // Outline's own custom icon set (camelCase keys).
+        "academicCap": "graduationcap.fill",
+        "bicycle": "bicycle",
+        "beaker": "testtube.2",
+        "buildingBlocks": "cube.fill",
+        "bookmark": "bookmark.fill",
+        "browser": "globe",
+        "collection": "square.grid.2x2.fill",
+        "coins": "dollarsign.circle.fill",
+        "camera": "camera.fill",
+        "carrot": "leaf.fill",
+        "clock": "clock.fill",
+        "cloud": "cloud.fill",
+        "code": "chevron.left.forwardslash.chevron.right",
+        "database": "cylinder.fill",
+        "done": "checkmark.circle.fill",
+        "email": "envelope.fill",
+        "eye": "eye.fill",
+        "feedback": "bubble.left.and.bubble.right.fill",
+        "flame": "flame.fill",
+        "graph": "chart.line.uptrend.xyaxis",
+        "globe": "globe",
+        "hashtag": "number",
+        "info": "info.circle.fill",
+        "image": "photo.fill",
+        "internet": "network",
+        "leaf": "leaf.fill",
+        "library": "books.vertical.fill",
+        "lightbulb": "lightbulb.fill",
+        "lightning": "bolt.fill",
+        "letter": "envelope.fill",
+        "math": "function",
+        "moon": "moon.fill",
+        "notepad": "note.text",
+        "padlock": "lock.fill",
+        "palette": "paintpalette.fill",
+        "pencil": "pencil",
+        "plane": "airplane",
+        "promote": "megaphone.fill",
+        "ramen": "fork.knife",
+        "question": "questionmark.circle.fill",
+        "server": "server.rack",
+        "sun": "sun.max.fill",
+        "shapes": "square.on.circle",
+        "sport": "sportscourt.fill",
+        "smiley": "face.smiling.fill",
+        "target": "target",
+        "team": "person.3.fill",
+        "terminal": "terminal.fill",
+        "thumbsup": "hand.thumbsup.fill",
+        "truck": "shippingbox.fill",
+        "tools": "wrench.and.screwdriver.fill",
+        "vehicle": "car.fill",
+        "warning": "exclamationmark.triangle.fill",
+
+        // FontAwesome icons (kebab-case keys) — high-confidence subset only.
+        "book": "book.fill",
+        "cake": "birthday.cake.fill",
+        "cat": "cat.fill",
+        "dog": "dog.fill",
+        "cube": "cube.fill",
+        "heart": "heart.fill",
+        "gift": "gift.fill",
+        "hammer": "hammer.fill",
+        "laptop": "laptopcomputer",
+        "map": "map.fill",
+        "newspaper": "newspaper.fill",
+        "paw": "pawprint.fill",
+        "shield": "shield.fill",
+        "tree": "tree.fill",
+        "trophy": "trophy.fill",
+        "umbrella": "umbrella.fill",
+        "fish": "fish.fill"
+    ]
+}
diff --git a/Outpost/Support/StarStore.swift b/Outpost/Support/StarStore.swift
new file mode 100644
index 0000000..05bac17
--- /dev/null
+++ b/Outpost/Support/StarStore.swift
@@ -0,0 +1,76 @@
+import Foundation
+import Observation
+import OutlineKit
+
+/// Shared starred-state cache, one `stars.list` fetch shared across every
+/// sidebar row and reader instead of each row independently guessing at its
+/// own starred state (the API has no `isStarred` field on `Document`/
+/// `Collection` themselves — the only source of truth is the stars list).
+@MainActor
+@Observable
+final class StarStore {
+    private var documentStars: [String: OutlineStar] = [:]
+    private var collectionStars: [String: OutlineStar] = [:]
+    private(set) var isLoaded = false
+
+    func isStarred(documentId: String) -> Bool {
+        documentStars[documentId] != nil
+    }
+
+    func isStarred(collectionId: String) -> Bool {
+        collectionStars[collectionId] != nil
+    }
+
+    func load(apiClient: OutlineAPIClient) async {
+        guard let stars = try? await apiClient.listStars(ListStarsRequest(offset: 0, limit: 250)) else { return }
+        documentStars = Dictionary(uniqueKeysWithValues: stars.compactMap { star in
+            star.documentId.map { ($0, star) }
+        })
+        collectionStars = Dictionary(uniqueKeysWithValues: stars.compactMap { star in
+            star.collectionId.map { ($0, star) }
+        })
+        isLoaded = true
+    }
+
+    func reset() {
+        documentStars = [:]
+        collectionStars = [:]
+        isLoaded = false
+    }
+
+    /// Optimistic — the row shows the new state immediately rather than
+    /// waiting on a re-fetch, then rolls back if the request actually fails.
+    func toggleDocument(_ documentId: String, apiClient: OutlineAPIClient) async throws {
+        if let star = documentStars[documentId] {
+            documentStars.removeValue(forKey: documentId)
+            do {
+                try await apiClient.deleteStar(id: star.id)
+            } catch {
+                documentStars[documentId] = star
+                throw error
+            }
+        } else {
+            do {
+                let star = try await apiClient.starDocument(StarDocumentRequest(documentId: documentId))
+                documentStars[documentId] = star
+            } catch {
+                throw error
+            }
+        }
+    }
+
+    func toggleCollection(_ collectionId: String, apiClient: OutlineAPIClient) async throws {
+        if let star = collectionStars[collectionId] {
+            collectionStars.removeValue(forKey: collectionId)
+            do {
+                try await apiClient.deleteStar(id: star.id)
+            } catch {
+                collectionStars[collectionId] = star
+                throw error
+            }
+        } else {
+            let star = try await apiClient.starCollection(StarCollectionRequest(collectionId: collectionId))
+            collectionStars[collectionId] = star
+        }
+    }
+}
diff --git a/Outpost/Support/View+LogoutConfirmation.swift b/Outpost/Support/View+LogoutConfirmation.swift
new file mode 100644
index 0000000..6675154
--- /dev/null
+++ b/Outpost/Support/View+LogoutConfirmation.swift
@@ -0,0 +1,18 @@
+import SwiftUI
+
+extension View {
+    func logoutConfirmationDialog(isPresented: Binding<Bool>, session: SessionStore) -> some View {
+        confirmationDialog(
+            "Log Out of Outpost?",
+            isPresented: isPresented,
+            titleVisibility: .visible
+        ) {
+            Button("Log Out", role: .destructive) {
+                session.signOut()
+            }
+            Button("Cancel", role: .cancel) {}
+        } message: {
+            Text("You'll need your server address and API token to sign in again.")
+        }
+    }
+}
diff --git a/Outpost/Support/WindowConfigurator.swift b/Outpost/Support/WindowConfigurator.swift
new file mode 100644
index 0000000..412325a
--- /dev/null
+++ b/Outpost/Support/WindowConfigurator.swift
@@ -0,0 +1,38 @@
+#if os(macOS)
+import SwiftUI
+import AppKit
+
+/// Grabs the hosting `NSWindow` once it's attached to a screen, for the
+/// handful of things SwiftUI's `Window` scene doesn't expose a modifier for.
+private struct WindowConfigurator: NSViewRepresentable {
+    let configure: (NSWindow) -> Void
+
+    func makeNSView(context: Context) -> NSView {
+        let view = NSView()
+        DispatchQueue.main.async {
+            if let window = view.window {
+                configure(window)
+            }
+        }
+        return view
+    }
+
+    func updateNSView(_ nsView: NSView, context: Context) {}
+}
+
+extension View {
+    /// `Window` scenes default to a full standard titlebar, fullscreen
+    /// (green) button included — not appropriate for fixed-size reference
+    /// panels like About or Keyboard Shortcuts, which have no reason to
+    /// support fullscreen at all.
+    func disablesFullScreen() -> some View {
+        background(
+            WindowConfigurator { window in
+                window.collectionBehavior.remove(.fullScreenPrimary)
+                window.collectionBehavior.insert(.fullScreenNone)
+                window.standardWindowButton(.zoomButton)?.isHidden = true
+            }
+        )
+    }
+}
+#endif
diff --git a/docs/ARCHITECTURE.md b/docs/ARCHITECTURE.md
index 60d8d05..4fea49f 100644
--- a/docs/ARCHITECTURE.md
+++ b/docs/ARCHITECTURE.md
@@ -8,6 +8,9 @@ Deeper technical reference backing `CLAUDE.md`. Update this as decisions are mad
 - **Auth**: `Authorization: Bearer <API_KEY>` header. Keys are created per-user under Settings → API Keys on the Outline instance. Store in Keychain, scope a dedicated key to this app rather than reusing a personal one.
 - **Core endpoints to wrap first**: `documents.info`, `documents.list`, `documents.search`, `documents.create`, `documents.update`, `collections.list`, `collections.info`, `users.info`.
 - Full reference: your instance's `/developers` page (same docs as getoutline.com/developers, versioned per Outline release — check against your self-hosted version, not just the public docs).
+- **Full OpenAPI spec, vendored as a git submodule**: [`docs/reference/outline-openapi`](reference/outline-openapi) → [`outline/openapi`](https://github.com/outline/openapi), spec at `docs/reference/outline-openapi/spec3.yml`. Check this before adding any new `OutlineAPIClient` method — read the exact request/response shape here rather than guessing from prose docs. It's already caught real mismatches twice: `documents.search`'s `sort` field rejects `"relevance"` as an explicit value even though the field is documented as accepting it (server only treats it as the implicit default when omitted), and `documents.search_titles` doesn't work against this self-hosted instance at all despite being in the spec (see `DocumentTitleSearchViewModel`'s doc comment — likely server version drift, matching the risk already called out below).
+  - Fresh clone: `git submodule update --init --recursive`.
+  - Refresh to upstream's latest: `git submodule update --remote docs/reference/outline-openapi`.
 
 ## 2. Realtime collaboration transport
 
diff --git a/docs/reference/outline-openapi b/docs/reference/outline-openapi
new file mode 160000
index 0000000..43d990d
--- /dev/null
+++ b/docs/reference/outline-openapi
@@ -0,0 +1 @@
+Subproject commit 43d990d5ec250e9f8daa05962d68b099128d2895
diff --git a/scripts/package-dmg.sh b/scripts/package-dmg.sh
new file mode 100755
index 0000000..babd9eb
--- /dev/null
+++ b/scripts/package-dmg.sh
@@ -0,0 +1,142 @@
+#!/bin/bash
+# Packages an already-exported Outpost.app into a distributable DMG with an
+# Applications-folder symlink for drag-to-install, then prints a Markdown
+# changelog to the terminal for pasting into the Gitea release notes —
+# nothing is written to the repo, this is generated fresh from git log
+# every time.
+#
+# Usage: scripts/package-dmg.sh /path/to/Outpost.app [output-dir]
+#
+# Produces: <output-dir>/Outpost-<version>.dmg
+# Version/build number are read directly from the app's own Info.plist, so
+# this always matches whatever MARKETING_VERSION was set to at archive time.
+
+set -euo pipefail
+
+APP_PATH="${1:?Usage: package-dmg.sh /path/to/Outpost.app [output-dir]}"
+OUT_DIR="${2:-$(pwd)/dist}"
+
+if [ ! -d "$APP_PATH" ]; then
+    echo "error: '$APP_PATH' not found or not a directory" >&2
+    exit 1
+fi
+
+APP_NAME="$(basename "$APP_PATH" .app)"
+VERSION="$(defaults read "$APP_PATH/Contents/Info" CFBundleShortVersionString)"
+BUILD="$(defaults read "$APP_PATH/Contents/Info" CFBundleVersion)"
+
+mkdir -p "$OUT_DIR"
+
+STAGING_DIR="$(mktemp -d)"
+trap 'rm -rf "$STAGING_DIR"' EXIT
+
+echo "Staging '$APP_NAME.app' ($VERSION build $BUILD)..."
+cp -R "$APP_PATH" "$STAGING_DIR/"
+ln -s /Applications "$STAGING_DIR/Applications"
+
+# Not notarized (no paid Apple Developer Program membership) — Gatekeeper
+# blocks it on a downloader's first launch. This is the standard bypass,
+# shipped in the DMG itself instead of repeated in every release's notes.
+cat > "$STAGING_DIR/Read Me First.txt" <<'EOF'
+Outpost isn't notarized by Apple (that requires a paid Apple Developer
+Program membership), so macOS Gatekeeper will block it on first launch
+with "cannot be opened because the developer cannot be verified."
+
+To open it anyway:
+  1. Drag Outpost.app to Applications.
+  2. Right-click (or Control-click) Outpost.app and choose "Open".
+  3. Click "Open" in the dialog that appears.
+
+You only need to do this once — after that it launches normally.
+
+If macOS instead shows "Outpost is damaged and can't be opened," that's
+the same Gatekeeper quarantine flag, just a different message on newer
+macOS versions. Fix it from Terminal:
+  xattr -cr /Applications/Outpost.app
+EOF
+
+DMG_NAME="${APP_NAME}-${VERSION}.dmg"
+DMG_PATH="$OUT_DIR/$DMG_NAME"
+rm -f "$DMG_PATH"
+
+echo "Building $DMG_NAME..."
+hdiutil create \
+    -volname "$APP_NAME $VERSION" \
+    -srcfolder "$STAGING_DIR" \
+    -ov \
+    -format UDZO \
+    "$DMG_PATH"
+
+echo "Done: $DMG_PATH"
+
+# --- Changelog -------------------------------------------------------------
+# Groups commits by conventional-commit type (feat/fix/.../other) between the
+# previous tag and whatever's being released. Two workflows are supported:
+#   - already tagged (HEAD == latest tag): diff against the tag before it.
+#   - not tagged yet (HEAD ahead of latest tag): diff since that tag.
+# Falls back to the full log if there are no tags at all yet.
+
+print_section() {
+    title="$1"
+    content="$2"
+    if [ -n "$content" ]; then
+        printf '### %s\n\n%s\n' "$title" "$content"
+    fi
+}
+
+REPO_ROOT="$(git rev-parse --show-toplevel 2>/dev/null || true)"
+if [ -z "$REPO_ROOT" ]; then
+    echo "" >&2
+    echo "warning: not inside a git repository, skipping changelog" >&2
+    exit 0
+fi
+
+LATEST_TAG="$(git -C "$REPO_ROOT" describe --tags --abbrev=0 2>/dev/null || true)"
+
+if [ -z "$LATEST_TAG" ]; then
+    RANGE="HEAD"
+    HEADING="Changelog"
+else
+    HEAD_COMMIT="$(git -C "$REPO_ROOT" rev-parse HEAD)"
+    TAG_COMMIT="$(git -C "$REPO_ROOT" rev-parse "$LATEST_TAG")"
+    if [ "$HEAD_COMMIT" = "$TAG_COMMIT" ]; then
+        PREV_TAG="$(git -C "$REPO_ROOT" describe --tags --abbrev=0 "${LATEST_TAG}^" 2>/dev/null || true)"
+        RANGE="${PREV_TAG:+$PREV_TAG..}$LATEST_TAG"
+        HEADING="Changelog ($LATEST_TAG)"
+    else
+        RANGE="$LATEST_TAG..HEAD"
+        HEADING="Changelog (since $LATEST_TAG)"
+    fi
+fi
+
+FEAT="" ; FIX="" ; PERF="" ; REFACTOR="" ; DOCS="" ; TESTS="" ; CHORE="" ; OTHER=""
+
+while IFS='|' read -r hash subject; do
+    [ -z "${hash:-}" ] && continue
+    case "$subject" in
+        feat*)     FEAT="${FEAT}- ${subject#*: } (${hash})"$'\n' ;;
+        fix*)      FIX="${FIX}- ${subject#*: } (${hash})"$'\n' ;;
+        perf*)     PERF="${PERF}- ${subject#*: } (${hash})"$'\n' ;;
+        refactor*) REFACTOR="${REFACTOR}- ${subject#*: } (${hash})"$'\n' ;;
+        docs*)     DOCS="${DOCS}- ${subject#*: } (${hash})"$'\n' ;;
+        test*)     TESTS="${TESTS}- ${subject#*: } (${hash})"$'\n' ;;
+        chore*)    CHORE="${CHORE}- ${subject#*: } (${hash})"$'\n' ;;
+        *)         OTHER="${OTHER}- ${subject} (${hash})"$'\n' ;;
+    esac
+done <<EOF
+$(git -C "$REPO_ROOT" log "$RANGE" --no-merges --pretty=format:'%h|%s' 2>/dev/null)
+EOF
+
+echo ""
+echo "---"
+echo ""
+echo "## $HEADING"
+echo ""
+print_section "Features" "$FEAT"
+print_section "Fixes" "$FIX"
+print_section "Performance" "$PERF"
+print_section "Refactors" "$REFACTOR"
+print_section "Documentation" "$DOCS"
+print_section "Tests" "$TESTS"
+print_section "Chores" "$CHORE"
+print_section "Other" "$OTHER"