feat: add Image Playground and fix Markdown image rendering

Image Playground integration: reader toolbar button ("Create Image
with Image Playground") opens the system generator, seeded with the
current text selection when there is one. Result uploads through the
same attachments.create/upload flow as everything else and inserts
Outline's own stable ![](/api/attachments.redirect?id=...) reference
at the caret, via a new generic TextInsertionRequest/
pendingTextInsertion mechanism on NativeTextViewWrapper (nothing
previously let an embedder insert text into the editor from outside
at all).

Along the way, found and fixed a real pre-existing gap: standard
![alt](url) Markdown images never rendered anywhere in the app -
services.images was never wired to anything but the no-op default, so
every such image silently fell back to dimmed raw source. Added
OutlineAPIClient.fetchAuthenticatedFile (Bearer-authed GET, for
attachments.redirect and similar) and OutlineImageProvider, a real
EmbeddedImageProvider backed by it, wired into every render surface
(reader, split-view preview, present sheet, collection overview).

Also fixes two Split View bugs surfaced while building this: the
raw-source pane was a plain SwiftUI TextEditor with no selection or
insertion hook, so the Image Playground button couldn't see a
highlighted selection there and generated images had nowhere to land;
replaced it with NativeTextViewWrapper in rawSourceMode (same engine,
no styling overhead, but now selection/insertion work like every
other pane). Also moved onSelectedTextChange's firing point earlier
in the delegate, since it was previously placed after the
rawSourceMode early-return and so could never fire for a raw-mode
editor at all. And images sized off a possibly-not-yet-settled text
container width during Split View's frequent per-keystroke rebuilds,
sticking at the wrong size until the document was reopened - now
re-measured once more a tick after layout settles.

Also reorganizes Settings: Command Palette and its full-workspace-
search toggle move out of Editor into a new Navigation section, since
they're about finding things, not about how documents are edited.

OutlineKit/Sources/OutlineKit/Caching/CachingOutlineAPIClient.swift

@@ -343,6 +343,10 @@ public actor CachingOutlineAPIClient: OutlineAPIClient {
         try await live.uploadAttachmentFile(result, fileData: fileData)
     }
 
+    public func fetchAuthenticatedFile(path: String) async throws -> Data {
+        try await live.fetchAuthenticatedFile(path: path)
+    }
+
     public func deleteAttachment(id: String) async throws {
         try await live.deleteAttachment(id: id)
     }

OutlineKit/Sources/OutlineKit/Core/OutlineAPIClient.swift

@@ -75,6 +75,14 @@ public protocol OutlineAPIClient: Sendable {
     /// target. See `OutlineAttachment`/`CreateAttachmentResult`.
     func createAttachment(_ request: CreateAttachmentRequest) async throws -> CreateAttachmentResult
     func uploadAttachmentFile(_ result: CreateAttachmentResult, fileData: Data) async throws
+    /// Fetches raw bytes from an authenticated, server-relative GET path —
+    /// e.g. `/api/attachments.redirect?id=<uuid>`, the reference Outline's
+    /// own editor embeds for uploaded images in document Markdown. Unlike
+    /// `post`'s RPC endpoints, this is a GET that 302-redirects to the
+    /// actual (often presigned, cross-host) storage URL; `path` is resolved
+    /// against the client's base URL, same as `uploadAttachmentFile`'s
+    /// `uploadUrl` handling.
+    func fetchAuthenticatedFile(path: String) async throws -> Data
     /// Best-effort — matches the shape every other simple `id`-only delete
     /// in this API uses (`pins.delete`, `stars.delete`, …), not confirmed
     /// against a live server specifically for attachments yet.

OutlineKit/Sources/OutlineKit/LiveOutlineAPIClient.swift

@@ -278,6 +278,45 @@ public actor LiveOutlineAPIClient: OutlineAPIClient {
         }
     }
 
+    public func fetchAuthenticatedFile(path: String) async throws -> Data {
+        guard let token = try? tokenStore.token() else {
+            throw OutlineAPIError.tokenUnavailable
+        }
+        // Same host-relative-or-absolute resolution as uploadAttachmentFile's uploadUrl.
+        guard let url = URL(string: path, relativeTo: baseURL)?.absoluteURL else {
+            throw OutlineAPIError.transport(URLError(.badURL))
+        }
+
+        var request = URLRequest(url: url)
+        // URLSession's default redirect handling drops Authorization on a
+        // cross-host redirect (same as a browser dropping cookies on one) —
+        // exactly what's wanted here: authorize the request to Outline's own
+        // `attachments.redirect`, not the presigned storage URL it 302s to.
+        request.setValue("Bearer \(token)", forHTTPHeaderField: "Authorization")
+
+        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 {
+            switch response.statusCode {
+            case 401:
+                throw OutlineAPIError.unauthorized
+            case 404:
+                throw OutlineAPIError.notFound
+            default:
+                throw OutlineAPIError.server(status: response.statusCode, message: nil)
+            }
+        }
+        return data
+    }
+
     public func deleteAttachment(id: String) async throws {
         try await postForSuccess("attachments.delete", body: StarIDParams(id: id))
     }

OutlineKit/Tests/OutlineKitTests/CachingOutlineAPIClientTests.swift

@@ -91,6 +91,7 @@ private final class StubOutlineAPIClient: OutlineAPIClient, @unchecked Sendable
     func currentUser() async throws -> OutlineUser { throw NotStubbed() }
     func createAttachment(_ request: CreateAttachmentRequest) async throws -> CreateAttachmentResult { throw NotStubbed() }
     func uploadAttachmentFile(_ result: CreateAttachmentResult, fileData: Data) async throws { throw NotStubbed() }
+    func fetchAuthenticatedFile(path: String) async throws -> Data { throw NotStubbed() }
     func deleteAttachment(id: String) async throws { throw NotStubbed() }
     func updateUserAvatar(_ request: UpdateUserAvatarRequest) async throws -> OutlineUser { throw NotStubbed() }
     func updateUserName(_ request: UpdateUserNameRequest) async throws -> OutlineUser { throw NotStubbed() }

Outpost/Features/Account/SettingsView.swift

@@ -17,6 +17,7 @@ struct SettingsView: View {
     @AppStorage("outpost.splitViewEnabled") private var isSplitViewEnabled = false
     @AppStorage("outpost.autocompleteEnabled") private var isAutocompleteEnabled = true
     @AppStorage("outpost.writingToolsEnabled") private var isWritingToolsEnabled = true
+    @AppStorage("outpost.imagePlaygroundEnabled") private var isImagePlaygroundEnabled = true
     @AppStorage("outpost.commandPaletteEnabled") private var isCommandPaletteEnabled = true
     @AppStorage("outpost.commandPaletteFullWorkspaceSearch") private var isCommandPaletteFullWorkspaceSearch = false
     @AppStorage(CachingOutlineAPIClient.offlineModeDefaultsKey) private var isOfflineModeEnabled = false
@@ -98,6 +99,7 @@ struct SettingsView: View {
         switch section {
         case .appearance: appearanceDetail
         case .editor: editorDetail
+        case .navigation: navigationDetail
         case .profile: profileDetail
         case .preferences: preferencesDetail
         case .notifications: notificationsDetail
@@ -188,6 +190,27 @@ struct SettingsView: View {
 
             Divider().frame(maxWidth: 480)
 
+            VStack(alignment: .leading, spacing: 6) {
+                Toggle("Image Playground", isOn: $isImagePlaygroundEnabled)
+                Text("Adds a \"Create Image with Image Playground\" button to the reader toolbar — generates an image from a text description (or your current selection, if any) and inserts it into the document. Requires macOS 15.1+ and a supported Mac — the toggle has no effect where it isn't available.")
+                    .font(.caption)
+                    .foregroundStyle(.secondary)
+            }
+            .frame(maxWidth: 480, alignment: .leading)
+        }
+    }
+
+    // MARK: - Navigation
+
+    /// Local-only settings for finding your way around the app — separate
+    /// from Editor, which is scoped to how documents are actually edited.
+    private var navigationDetail: some View {
+        VStack(alignment: .leading, spacing: 16) {
+            sectionHeader
+            Text("Settings for finding documents and collections.")
+                .font(.subheadline)
+                .foregroundStyle(.secondary)
+
             VStack(alignment: .leading, spacing: 6) {
                 Toggle("Command Palette", isOn: $isCommandPaletteEnabled)
                 Text("Press ⌘K to quickly jump to a document or collection. Always searches locally on your device — never a network request while typing.")

Outpost/Features/Collections/CollectionOverviewContent.swift

@@ -10,9 +10,13 @@ import OutlineKit
 /// `isSelectable` and link-opening both still need to work.
 struct CollectionOverviewContent: View {
     @State private var markdown: String
+    @State private var imageProvider: OutlineImageProvider
+    /// See `DocumentReaderView`'s `imageReloadTick`.
+    @State private var imageReloadTick = 0
 
-    init(collection: OutlineCollection) {
+    init(apiClient: OutlineAPIClient, collection: OutlineCollection) {
         _markdown = State(initialValue: collection.description ?? "")
+        _imageProvider = State(initialValue: OutlineImageProvider(apiClient: apiClient))
     }
 
     var body: some View {
@@ -20,7 +24,7 @@ struct CollectionOverviewContent: View {
             NativeTextViewWrapper(
                 text: $markdown,
                 configuration: .init(
-                    services: .init(syntaxHighlighter: CodeSyntaxHighlighting.shared),
+                    services: .init(images: imageProvider, syntaxHighlighter: CodeSyntaxHighlighting.shared),
                     heightBehavior: .fitsContent
                 ),
                 isEditable: false
@@ -28,6 +32,12 @@ struct CollectionOverviewContent: View {
             .padding()
         }
         .frame(maxWidth: .infinity, maxHeight: .infinity, alignment: .topLeading)
+        .animation(nil, value: imageReloadTick)
+        .task {
+            imageProvider.onImageLoaded = {
+                Task { @MainActor in imageReloadTick += 1 }
+            }
+        }
     }
 }
 #endif

Outpost/Features/Collections/CollectionOverviewView.swift

@@ -3,6 +3,7 @@ import SwiftUI
 import OutlineKit
 
 struct CollectionOverviewView: View {
+    let apiClient: OutlineAPIClient
     let collection: OutlineCollection
     @State private var viewModel: DocumentsViewModel
     @State private var selectedTab: CollectionTab = .overview
@@ -25,6 +26,7 @@ struct CollectionOverviewView: View {
         searchQuery: Binding<String>,
         onOpenDocument: @escaping (OutlineDocument) -> Void
     ) {
+        self.apiClient = apiClient
         self.collection = collection
         _viewModel = State(initialValue: DocumentsViewModel(apiClient: apiClient, collection: collection))
         _searchViewModel = State(initialValue: DocumentTitleSearchViewModel(apiClient: apiClient, collectionId: collection.id))
@@ -59,7 +61,7 @@ struct CollectionOverviewView: View {
                 if !trimmedSearchQuery.isEmpty {
                     searchResultsList
                 } else if selectedTab == .overview {
-                    CollectionOverviewContent(collection: collection)
+                    CollectionOverviewContent(apiClient: apiClient, collection: collection)
                 } else {
                     documentList
                 }

Outpost/Features/Collections/DocumentPresentSheet.swift

@@ -17,11 +17,17 @@ struct DocumentPresentSheet: View {
     @State private var text: String
     @State private var isLoading = false
     @State private var errorMessage: String?
+    @State private var imageProvider: OutlineImageProvider
+    /// See `DocumentReaderView`'s `imageReloadTick` — same "force an
+    /// `updateNSView` re-pass so the engine notices `fingerprint()` changed"
+    /// mechanism, needed here too since this sheet renders its own images.
+    @State private var imageReloadTick = 0
 
     init(apiClient: OutlineAPIClient, document: OutlineDocument) {
         self.apiClient = apiClient
         self.document = document
         _text = State(initialValue: document.text)
+        _imageProvider = State(initialValue: OutlineImageProvider(apiClient: apiClient))
     }
 
     var body: some View {
@@ -46,7 +52,7 @@ struct DocumentPresentSheet: View {
                         NativeTextViewWrapper(
                             text: $text,
                             configuration: .init(
-                                services: .init(syntaxHighlighter: CodeSyntaxHighlighting.shared),
+                                services: .init(images: imageProvider, syntaxHighlighter: CodeSyntaxHighlighting.shared),
                                 heightBehavior: .fitsContent
                             ),
                             isEditable: false
@@ -71,6 +77,12 @@ struct DocumentPresentSheet: View {
         }
         .frame(minWidth: 800, minHeight: 600)
         .background(.background)
+        .animation(nil, value: imageReloadTick)
+        .task {
+            imageProvider.onImageLoaded = {
+                Task { @MainActor in imageReloadTick += 1 }
+            }
+        }
         .task { await load() }
     }
 

Outpost/Features/Collections/DocumentReaderView.swift

@@ -5,6 +5,9 @@ import UniformTypeIdentifiers
 import MarkdownEngine
 import MarkdownEngineCodeBlocks
 import OutlineKit
+#if canImport(ImagePlayground)
+import ImagePlayground
+#endif
 
 /// `NSSavePanel`/`NSPrintOperation`/`NSPasteboard` in the action functions
 /// below must run on the main thread — see the identical note on
@@ -19,6 +22,20 @@ struct DocumentReaderView: View {
     @AppStorage("outpost.splitViewEnabled") private var isSplitViewEnabled = false
     @AppStorage("outpost.autocompleteEnabled") private var isAutocompleteEnabled = true
     @AppStorage("outpost.writingToolsEnabled") private var isWritingToolsEnabled = true
+    @AppStorage("outpost.imagePlaygroundEnabled") private var isImagePlaygroundEnabled = true
+
+    /// `ImagePlaygroundViewController.isAvailable` gates on both OS version
+    /// (macOS 15.1+) and actual device/region support (Apple Intelligence
+    /// eligibility) — a supported OS with an unsupported Mac still reports
+    /// `false`, so this is the one check that matters, not just `#available`.
+    private var isImagePlaygroundSupported: Bool {
+        #if canImport(ImagePlayground)
+        if #available(macOS 15.1, *) {
+            return ImagePlaygroundViewController.isAvailable
+        }
+        #endif
+        return false
+    }
 
     /// Outline's own "Show line numbers" preference (synced, read via
     /// `session.userPreferences`, not `@AppStorage` — this one's the
@@ -75,7 +92,27 @@ struct DocumentReaderView: View {
     @State private var isShowingSearchSheet = false
     @State private var isShowingShareSheet = false
     @State private var isShowingNewDocumentSheet = false
+    @State private var isShowingImagePlayground = false
     @State private var actionErrorMessage: String?
+    /// Pushed into the main editable pane's `NativeTextViewWrapper` to
+    /// insert an Image Playground result's Markdown reference at the caret.
+    @State private var pendingTextInsertion: TextInsertionRequest?
+    /// Live-updated by `onSelectedTextChange` on the main editable pane;
+    /// `nil` when the selection is empty (caret only, nothing highlighted).
+    @State private var currentSelectedText: String?
+    /// Resolves `![alt](url)` images in this document — shared by both
+    /// panes (main + split-view preview), since they render the same text.
+    @State private var imageProvider: OutlineImageProvider
+    /// Bumped by `imageProvider.onImageLoaded`. Not read for its value —
+    /// just referenced via `.animation(nil, value:)` so SwiftUI re-evaluates
+    /// this view (and so `NativeTextViewWrapper.updateNSView` re-runs and
+    /// notices the provider's `fingerprint()` changed) once an async image
+    /// load completes. The engine has no polling of its own for this.
+    @State private var imageReloadTick = 0
+    /// Snapshot of `currentSelectedText` taken the moment the Image
+    /// Playground button is pressed — the sheet's seed shouldn't shift if
+    /// the user's selection happens to change while it's open.
+    @State private var imagePlaygroundSeedText: String?
     /// Populated live by `NativeTextViewWrapper`'s `onCodeBlockSelectionChange` —
     /// one array per instance (main pane, split-view preview pane), since
     /// each lays the same text out at a different width and gets different
@@ -100,6 +137,7 @@ struct DocumentReaderView: View {
         // behavior) and gets set for real in `.task` below once `session`
         // is actually available.
         _viewModel = State(initialValue: DocumentReaderViewModel(apiClient: apiClient, document: document))
+        _imageProvider = State(initialValue: OutlineImageProvider(apiClient: apiClient))
         self.onOpenChild = onOpenChild
         self.onDeleted = onDeleted
         self.onDocumentCreated = onDocumentCreated
@@ -157,6 +195,17 @@ struct DocumentReaderView: View {
                     DocumentShareSheet(apiClient: apiClient, documentId: viewModel.documentId)
                 }
 
+                if isImagePlaygroundEnabled && isImagePlaygroundSupported {
+                    Button {
+                        imagePlaygroundSeedText = currentSelectedText
+                        isShowingImagePlayground = true
+                    } label: {
+                        Image(systemName: "sparkles")
+                    }
+                    .help("Create Image with Image Playground")
+                    .disabled(!viewModel.isEffectivelyEditable)
+                }
+
                 if viewModel.separateEditingEnabled {
                     Button {
                         Task { await viewModel.toggleEditing() }
@@ -197,6 +246,12 @@ struct DocumentReaderView: View {
                 .id(menuIdentity)
             }
         }
+        .task {
+            imageProvider.onImageLoaded = {
+                Task { @MainActor in imageReloadTick += 1 }
+            }
+        }
+        .animation(nil, value: imageReloadTick)
         .task { await viewModel.loadFullContent() }
         // See the doc comment on `DocumentReaderViewModel.separateEditingEnabled`
         // for why this can't just be read at `init` time.
@@ -285,6 +340,41 @@ struct DocumentReaderView: View {
                 onOpenChild(child)
             }
         }
+        .modifier(ImagePlaygroundPresenter(
+            isPresented: $isShowingImagePlayground,
+            seedText: imagePlaygroundSeedText,
+            seedTitle: viewModel.title.isEmpty ? "Untitled" : viewModel.title,
+            onCompletion: { url in handleGeneratedImage(url) }
+        ))
+    }
+
+    /// Uploads an Image Playground result the same way the reader would any
+    /// other attachment (`attachments.create` presigned target, then the
+    /// direct file POST — see `OutlineAPIClient.uploadAttachmentFile`), then
+    /// inserts the hosted image's Markdown reference at the caret.
+    private func handleGeneratedImage(_ localURL: URL) {
+        Task {
+            do {
+                let data = try Data(contentsOf: localURL)
+                let created = try await apiClient.createAttachment(.init(
+                    name: localURL.lastPathComponent,
+                    contentType: "image/png",
+                    size: data.count,
+                    documentId: viewModel.documentId
+                ))
+                try await apiClient.uploadAttachmentFile(created, fileData: data)
+                // Outline's own editor never embeds the raw (presigned/storage)
+                // upload URL in document Markdown — it writes this stable
+                // redirect-by-id reference instead, which keeps resolving
+                // correctly even if the underlying storage URL rotates/expires.
+                pendingTextInsertion = TextInsertionRequest(
+                    documentId: viewModel.documentId,
+                    text: "\n\n![](/api/attachments.redirect?id=\(created.attachment.id))\n\n"
+                )
+            } catch {
+                actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't add the generated image.")
+            }
+        }
     }
 
     /// Every toggle-backed piece of state shown as a checkmark inside
@@ -350,8 +440,9 @@ struct DocumentReaderView: View {
                     ZStack(alignment: .topLeading) {
                         NativeTextViewWrapper(
                             text: $viewModel.text,
+                            pendingTextInsertion: $pendingTextInsertion,
                             configuration: .init(
-                                services: .init(syntaxHighlighter: CodeSyntaxHighlighting.shared),
+                                services: .init(images: imageProvider, syntaxHighlighter: CodeSyntaxHighlighting.shared),
                                 codeBlock: editorCodeBlockStyle,
                                 textSubstitution: editorTextSubstitution,
                                 textCompletion: editorTextCompletion,
@@ -360,7 +451,8 @@ struct DocumentReaderView: View {
                             ),
                             documentId: viewModel.documentId,
                             isEditable: viewModel.isEffectivelyEditable,
-                            onCodeBlockSelectionChange: { readerCodeBlocks = $0 }
+                            onCodeBlockSelectionChange: { readerCodeBlocks = $0 },
+                            onSelectedTextChange: { currentSelectedText = $0 }
                         )
                         if showCodeBlockLineNumbers {
                             ForEach(readerCodeBlocks) { selection in
@@ -394,11 +486,13 @@ struct DocumentReaderView: View {
         }
     }
 
-    /// Left is a plain, unrendered raw-text editor (deliberately not
-    /// `NativeTextViewWrapper` — just the literal Markdown source); right
-    /// is the same rich rendering used everywhere else in the app,
-    /// read-only, bound to the same `viewModel.text` so it updates live as
-    /// the left side is typed into.
+    /// Left is the literal Markdown source in `rawSourceMode` (no syntax
+    /// hiding/styling, but still the real engine — needed so selection
+    /// tracking and caret-position insertion, e.g. from the Image Playground
+    /// button, work here the same as everywhere else); right is the same
+    /// rich rendering used everywhere else in the app, read-only, bound to
+    /// the same `viewModel.text` so it updates live as the left side is
+    /// typed into.
     ///
     /// Scroll position between the two panes is **not** synchronized — the
     /// only way to do that would be reaching into `NativeTextViewWrapper`'s
@@ -408,24 +502,31 @@ struct DocumentReaderView: View {
     /// follow-up, not attempted here.
     private var splitEditorView: some View {
         HSplitView {
-            TextEditor(text: $viewModel.text)
-                .font(.system(.body, design: .monospaced))
-                .scrollContentBackground(.hidden)
-                .padding(8)
-                .frame(minWidth: 300, maxWidth: .infinity, maxHeight: .infinity)
+            NativeTextViewWrapper(
+                text: $viewModel.text,
+                pendingTextInsertion: $pendingTextInsertion,
+                configuration: .init(rawSourceMode: true),
+                fontName: "SFMono-Regular",
+                documentId: viewModel.documentId,
+                isEditable: viewModel.isEffectivelyEditable,
+                onSelectedTextChange: { currentSelectedText = $0 }
+            )
+            .padding(8)
+            .frame(minWidth: 300, maxWidth: .infinity, maxHeight: .infinity)
 
             ScrollView {
                 ZStack(alignment: .topLeading) {
                     NativeTextViewWrapper(
                         text: $viewModel.text,
                         configuration: .init(
-                            services: .init(syntaxHighlighter: CodeSyntaxHighlighting.shared),
+                            services: .init(images: imageProvider, syntaxHighlighter: CodeSyntaxHighlighting.shared),
                             codeBlock: editorCodeBlockStyle,
                             heightBehavior: .fitsContent
                         ),
                         documentId: viewModel.documentId,
                         isEditable: false,
-                        onCodeBlockSelectionChange: { previewCodeBlocks = $0 }
+                        onCodeBlockSelectionChange: { previewCodeBlocks = $0 },
+                        onSelectedTextChange: { currentSelectedText = $0 }
                     )
                     if showCodeBlockLineNumbers {
                         ForEach(previewCodeBlocks) { selection in
@@ -731,4 +832,44 @@ private struct CodeBlockLineNumberGutter: View {
         .allowsHitTesting(false)
     }
 }
+
+/// Applies `.imagePlaygroundSheet` only where it exists (macOS 15.1+, and
+/// only once the `ImagePlayground` framework is actually linked in Xcode —
+/// see `SETUP.md`). A no-op modifier everywhere else, so this file stays
+/// valid to build before that link-up happens.
+private struct ImagePlaygroundPresenter: ViewModifier {
+    @Binding var isPresented: Bool
+    /// Highlighted document text at the moment the button was pressed, if
+    /// any — seeds Image Playground's prompt instead of opening blank.
+    let seedText: String?
+    /// Document title, used as the concept's title when `seedText` is used.
+    let seedTitle: String
+    let onCompletion: (URL) -> Void
+
+    func body(content: Content) -> some View {
+        #if canImport(ImagePlayground)
+        if #available(macOS 15.1, *) {
+            let concepts: [ImagePlaygroundConcept] = {
+                guard let seedText, !seedText.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty else {
+                    return []
+                }
+                return [ImagePlaygroundConcept.extracted(from: seedText, title: seedTitle)]
+            }()
+            content.imagePlaygroundSheet(
+                isPresented: $isPresented,
+                concepts: concepts,
+                onCompletion: { url in
+                    isPresented = false
+                    onCompletion(url)
+                },
+                onCancellation: { isPresented = false }
+            )
+        } else {
+            content
+        }
+        #else
+        content
+        #endif
+    }
+}
 #endif

Outpost/Root/AppNavigation.swift

@@ -33,7 +33,7 @@ enum SettingsCategory: String, CaseIterable, Identifiable {
 /// explicitly built yet. Content lands section by section.
 enum SettingsSection: String, CaseIterable, Identifiable, Hashable {
     // General (ours)
-    case appearance, editor, offlineSync, advanced, about
+    case appearance, editor, navigation, offlineSync, advanced, about
 
     // Account
     case profile, preferences, notifications, passkeys, apiAccess
@@ -45,7 +45,7 @@ enum SettingsSection: String, CaseIterable, Identifiable, Hashable {
 
     var category: SettingsCategory {
         switch self {
-        case .appearance, .editor, .offlineSync, .advanced, .about:
+        case .appearance, .editor, .navigation, .offlineSync, .advanced, .about:
             return .general
         case .profile, .preferences, .notifications, .passkeys, .apiAccess:
             return .account
@@ -58,6 +58,7 @@ enum SettingsSection: String, CaseIterable, Identifiable, Hashable {
         switch self {
         case .appearance: return "Appearance"
         case .editor: return "Editor"
+        case .navigation: return "Navigation"
         case .offlineSync: return "Offline & Sync"
         case .advanced: return "Advanced"
         case .about: return "About"
@@ -87,6 +88,7 @@ enum SettingsSection: String, CaseIterable, Identifiable, Hashable {
         switch self {
         case .appearance: return "paintbrush"
         case .editor: return "square.split.2x1"
+        case .navigation: return "command"
         case .offlineSync: return "arrow.triangle.2.circlepath"
         case .advanced: return "wrench.and.screwdriver"
         case .about: return "info.circle"
@@ -117,7 +119,7 @@ enum SettingsSection: String, CaseIterable, Identifiable, Hashable {
     /// specified and built.
     var isImplemented: Bool {
         switch self {
-        case .appearance, .editor, .offlineSync, .advanced, .about, .profile, .preferences, .notifications, .passkeys, .apiAccess:
+        case .appearance, .editor, .navigation, .offlineSync, .advanced, .about, .profile, .preferences, .notifications, .passkeys, .apiAccess:
             return true
         default:
             return false

Outpost/Support/OutlineImageProvider.swift

@@ -0,0 +1,84 @@
+#if os(macOS)
+import AppKit
+import MarkdownEngine
+import OutlineKit
+
+/// Resolves `![alt](url)` Markdown image references for the editor.
+///
+/// `EmbeddedImageProvider.image(for:)` is called synchronously from the
+/// styling pipeline and must return immediately — it can't `await` a
+/// network fetch inline. So a miss kicks off an async load in the
+/// background, caches the result, and calls `onImageLoaded` (on the main
+/// thread) once it lands; the embedder is responsible for turning that into
+/// a real SwiftUI update (see `DocumentReaderView`'s `imageReloadTick`) so
+/// `updateNSView` runs again, notices `fingerprint()` changed, and
+/// restyles — the engine has no polling of its own.
+///
+/// `url` is usually a server-relative path like
+/// `/api/attachments.redirect?id=<uuid>` — Outline's own stable reference
+/// for an uploaded attachment, which needs the same Bearer auth as every
+/// other OutlineKit request (`OutlineAPIClient.fetchAuthenticatedFile`).
+/// A plain absolute `http(s)://` URL (an external image someone pasted) is
+/// fetched directly instead, no auth attached.
+///
+/// Thread-safety mirrors `HighlighterSwiftBridge`: `NSCache` for the image
+/// store (inherently thread-safe), a lock for the small bit of state that
+/// isn't (`version`, `inFlight`) — no actor isolation, since the engine may
+/// call `image(for:)`/`fingerprint()` from whatever thread is styling.
+final class OutlineImageProvider: EmbeddedImageProvider, @unchecked Sendable {
+    private let apiClient: OutlineAPIClient
+    private let cache = NSCache<NSString, NSImage>()
+    private let lock = NSLock()
+    private var inFlight: Set<String> = []
+    private var version = 0
+    /// Set by the embedder; called on the main thread whenever a load
+    /// completes and `fingerprint()` has changed.
+    var onImageLoaded: (@Sendable () -> Void)?
+
+    init(apiClient: OutlineAPIClient) {
+        self.apiClient = apiClient
+    }
+
+    func image(for reference: EmbeddedImageRequest) -> NSImage? {
+        let url = reference.name
+        if let cached = cache.object(forKey: url as NSString) {
+            return cached
+        }
+        beginLoad(url)
+        return nil
+    }
+
+    func fingerprint() -> AnyHashable {
+        lock.withLock { version }
+    }
+
+    private func beginLoad(_ url: String) {
+        let alreadyLoading: Bool = lock.withLock {
+            if inFlight.contains(url) { return true }
+            inFlight.insert(url)
+            return false
+        }
+        guard !alreadyLoading else { return }
+
+        Task {
+            defer { lock.withLock { inFlight.remove(url) } }
+            do {
+                let data: Data
+                if url.hasPrefix("http://") || url.hasPrefix("https://"), let externalURL = URL(string: url) {
+                    (data, _) = try await URLSession.shared.data(from: externalURL)
+                } else {
+                    data = try await apiClient.fetchAuthenticatedFile(path: url)
+                }
+                guard let image = NSImage(data: data) else { return }
+                cache.setObject(image, forKey: url as NSString)
+                lock.withLock { version += 1 }
+                onImageLoaded?()
+            } catch {
+                // Best-effort: a failed load just leaves the Markdown source
+                // visible (the engine's existing fallback for `image(for:)
+                // == nil`), no separate error UI for an inline image fetch.
+            }
+        }
+    }
+}
+#endif

Vendor/swift-markdown-engine/Sources/MarkdownEngine/TextView/Coordinator/NativeTextViewCoordinator+Restyling.swift

@@ -200,6 +200,31 @@ extension NativeTextViewCoordinator {
                 nativeTextView?.updateWideTableOverlays()
             }
         }
+
+        // Standalone images (`![alt](url)`/`![[embed]]`) size themselves off
+        // the text container's width AT THIS MOMENT (see styleImageLinks/
+        // styleImageEmbeds' maxWidth) — every keystroke rebuilds this whole
+        // pane when it's a read-only mirror of another editable view driving
+        // the same `text` binding (e.g. Split View's preview pane), and mid-
+        // typing the container can be reflowing (HSplitView divider, a
+        // `.fitsContent` pane still resizing) and read too small/zero for a
+        // moment. That undersized measurement then just sticks — nothing
+        // else re-triggers a restyle once typing stops and the fingerprint-
+        // based image-load path (see NativeTextViewWrapper's `imageChanged`
+        // handling) doesn't fire for an already-cached image. Re-measure
+        // once more, one tick later, only when there's actually an image in
+        // the document — same fix shape as the wide-table reconciliation
+        // above, just for image sizing instead of overlay frames.
+        let hasImages = (parsedForReplay?.classified.imageLink.isEmpty == false)
+            || (parsedForReplay?.classified.imageEmbed.isEmpty == false)
+        if hasImages {
+            DispatchQueue.main.async { [weak self, weak textView] in
+                guard let self, let textView else { return }
+                let range = NSRange(location: 0, length: (textView.string as NSString).length)
+                guard range.length > 0 else { return }
+                self.restyleParagraphs([range], in: textView)
+            }
+        }
     }
 
     func restyleTextView(
@@ -417,6 +442,33 @@ extension NativeTextViewCoordinator {
                         classified: parsed.classified, blocks: parsed.blocks)
     }
 
+    /// Inserts `request.text` at the current caret (replacing the selection,
+    /// if any) as a normal undoable edit. Simpler than
+    /// ``applyInlineReplacement(_:to:)`` — no inline-token range, no
+    /// wiki-link ID side-channel, just a plain insert.
+    func applyTextInsertion(_ request: TextInsertionRequest, to textView: NSTextView) {
+        lastAppliedTextInsertionID = request.id
+
+        let range = textView.selectedRange()
+        textView.breakUndoCoalescing()
+
+        isProgrammaticEdit = true
+        defer { isProgrammaticEdit = false }
+
+        guard textView.shouldChangeText(in: range, replacementString: request.text) else {
+            return
+        }
+
+        textView.textStorage?.replaceCharacters(in: range, with: request.text)
+        textView.didChangeText()
+        textView.undoManager?.setActionName("Insert Image")
+        textView.breakUndoCoalescing()
+
+        let documentLength = (textView.string as NSString).length
+        let caretLocation = min(range.location + (request.text as NSString).length, documentLength)
+        textView.setSelectedRange(NSRange(location: caretLocation, length: 0))
+    }
+
     func applyInlineReplacement(_ request: InlineReplacementRequest, to textView: NSTextView) {
         lastAppliedInlineReplacementID = request.id
 

Vendor/swift-markdown-engine/Sources/MarkdownEngine/TextView/Coordinator/NativeTextViewCoordinator+TextDelegate.swift

@@ -355,6 +355,14 @@ extension NativeTextViewCoordinator {
 
     public func textViewDidChangeSelection(_ notification: Notification) {
         guard let tv = notification.object as? NSTextView else { return }
+        // Cheap and mode-independent — fire before the raw-mode/rebuild
+        // early-returns below, which would otherwise mean a `rawSourceMode`
+        // editor (e.g. Split View's raw-source pane) never reports a
+        // selection at all.
+        if !isRebuildingDocument {
+            let selRange = tv.selectedRange()
+            onSelectedTextChange?(selRange.length > 0 ? (tv.string as NSString).substring(with: selRange) : nil)
+        }
         // Raw mode: plain source — no reveal, snap-back, or inline previews.
         if configuration.rawSourceMode { return }
         if isWritingToolsActive { return }

Vendor/swift-markdown-engine/Sources/MarkdownEngine/TextView/Coordinator/NativeTextViewCoordinator.swift

@@ -84,6 +84,7 @@ public final class NativeTextViewCoordinator: NSObject, NSTextViewDelegate {
     var onInlineSelectionChange: ((InlineSelectionState?) -> Void)?
     var onInlinePreviewKey: ((InlinePreviewKey) -> Bool)?
     var onCodeBlockSelectionChange: (([CodeBlockSelection]) -> Void)?
+    var onSelectedTextChange: ((String?) -> Void)?
     var didInitialFormatting: Bool = false
     /// One-shot guard so `updateCodeBlockSelection` only forces a full-document layout once per document.
     var didEnsureLayoutForCurrentDocument: Bool = false
@@ -106,6 +107,7 @@ public final class NativeTextViewCoordinator: NSObject, NSTextViewDelegate {
     var wtUndoneDuringSession: Bool = false
     var wtPostUndoSnapshot: String?
     var lastAppliedInlineReplacementID: UUID?
+    var lastAppliedTextInsertionID: UUID?
     var activeTokenIndices: Set<Int> = []
     var previousActiveTokenIndices: Set<Int> = []
     var wikiLinkMetadata: [WikiLinkService.RangeKey: WikiLinkService.LinkMetadata] = [:]

Vendor/swift-markdown-engine/Sources/MarkdownEngine/TextView/NativeTextViewSelectionTypes.swift

@@ -93,3 +93,30 @@ public struct InlineReplacementRequest: Sendable {
         self.isImageEmbedMode = isImageEmbedMode
     }
 }
+
+/// Request to insert literal text at the current caret (replacing the
+/// current selection, if any) — e.g. a Markdown image reference from an
+/// embedder-side image picker or generator.
+///
+/// Embedders push one of these into
+/// ``NativeTextViewWrapper/pendingTextInsertion`` to commit it. The engine
+/// inserts it as a normal (undoable) edit, moves the caret past it, and
+/// clears the binding. Unlike ``InlineReplacementRequest``, this doesn't
+/// target an existing inline token — it just inserts at wherever the caret
+/// currently is.
+public struct TextInsertionRequest: Sendable {
+    /// Stable identifier so the engine can detect already-applied requests
+    /// across SwiftUI re-renders.
+    public let id: UUID
+    /// Document the insertion targets. Ignored if it doesn't match the
+    /// editor's current `documentId` (prevents cross-document writes).
+    public let documentId: String
+    /// Storage-form text to insert at the caret.
+    public let text: String
+
+    public init(id: UUID = UUID(), documentId: String, text: String) {
+        self.id = id
+        self.documentId = documentId
+        self.text = text
+    }
+}

Vendor/swift-markdown-engine/Sources/MarkdownEngine/TextView/NativeTextViewWrapper.swift

@@ -55,6 +55,10 @@ public struct NativeTextViewWrapper: NSViewRepresentable {
     /// Push a replacement into the editor by setting this to a non-nil value;
     /// the engine applies it on the next update and then clears the binding.
     @Binding public var pendingInlineReplacement: InlineReplacementRequest?
+    /// Push a plain-text insertion at the caret by setting this to a non-nil
+    /// value; the engine applies it on the next update and then clears the
+    /// binding. See ``TextInsertionRequest``.
+    @Binding public var pendingTextInsertion: TextInsertionRequest?
     /// The full editor configuration (theme + services + style toggles). Engine
     /// embedders construct this themselves and pass it in; the wrapper does
     /// not read UserDefaults or know about app-specific colors/services.
@@ -95,6 +99,11 @@ public struct NativeTextViewWrapper: NSViewRepresentable {
     /// Fires when the set of visible code blocks changes, so embedders can
     /// overlay copy buttons (see ``CodeBlockButton``).
     public var onCodeBlockSelectionChange: (([CodeBlockSelection]) -> Void)?
+    /// Fires whenever the text selection changes. `nil` for an empty (caret-only)
+    /// selection, otherwise the plain-text substring currently selected — useful
+    /// for embedder features that act on "whatever's selected" (e.g. seeding a
+    /// generator's prompt).
+    public var onSelectedTextChange: ((String?) -> Void)?
     /// Fires after the user toggles any of the three spell/grammar/auto-correction
     /// menu items. Embedders persist the policy and pass it back via
     /// ``MarkdownEditorConfiguration/spellChecking`` on next launch.
@@ -141,6 +150,7 @@ public struct NativeTextViewWrapper: NSViewRepresentable {
         text: Binding<String>,
         isWikiLinkActive: Binding<Bool> = .constant(false),
         pendingInlineReplacement: Binding<InlineReplacementRequest?> = .constant(nil),
+        pendingTextInsertion: Binding<TextInsertionRequest?> = .constant(nil),
         configuration: MarkdownEditorConfiguration = .default,
         fontName: String = "SF Pro",
         fontSize: CGFloat = 16,
@@ -153,6 +163,7 @@ public struct NativeTextViewWrapper: NSViewRepresentable {
         onInlineSelectionChange: ((InlineSelectionState?) -> Void)? = nil,
         onInlinePreviewKey: ((InlinePreviewKey) -> Bool)? = nil,
         onCodeBlockSelectionChange: (([CodeBlockSelection]) -> Void)? = nil,
+        onSelectedTextChange: ((String?) -> Void)? = nil,
         onSpellCheckingPolicyChanged: ((SpellCheckingPolicy) -> Void)? = nil,
         placeholder: NSAttributedString? = nil,
         header: AnyView? = nil,
@@ -166,6 +177,7 @@ public struct NativeTextViewWrapper: NSViewRepresentable {
         self._text = text
         self._isWikiLinkActive = isWikiLinkActive
         self._pendingInlineReplacement = pendingInlineReplacement
+        self._pendingTextInsertion = pendingTextInsertion
         self.configuration = configuration
         self.fontName = fontName
         self.fontSize = fontSize
@@ -178,6 +190,7 @@ public struct NativeTextViewWrapper: NSViewRepresentable {
         self.onInlineSelectionChange = onInlineSelectionChange
         self.onInlinePreviewKey = onInlinePreviewKey
         self.onCodeBlockSelectionChange = onCodeBlockSelectionChange
+        self.onSelectedTextChange = onSelectedTextChange
         self.onSpellCheckingPolicyChanged = onSpellCheckingPolicyChanged
         self.placeholder = placeholder
         self.header = header
@@ -328,6 +341,7 @@ public struct NativeTextViewWrapper: NSViewRepresentable {
         context.coordinator.onInlineSelectionChange = onInlineSelectionChange
         context.coordinator.onInlinePreviewKey = onInlinePreviewKey
         context.coordinator.onCodeBlockSelectionChange = onCodeBlockSelectionChange
+        context.coordinator.onSelectedTextChange = onSelectedTextChange
 
         textView.recalcOverscroll(for: scrollView)
         textView.setPlaceholder(placeholder)
@@ -541,6 +555,26 @@ public struct NativeTextViewWrapper: NSViewRepresentable {
             if fullRange.length > 0 {
                 context.coordinator.restyleParagraphs([fullRange], in: textView)
             }
+            // An image's display width is measured off the text container's
+            // CURRENT width (see styleImageLinks/styleImageEmbeds' maxWidth),
+            // which may not have settled to its real value yet in this same
+            // pass — e.g. right after a text change that also grows/shrinks
+            // the pane (Split View's HSplitView reflow, `.fitsContent`
+            // resizing). A too-small width here falls back to a small
+            // default and, with nothing else in this document changing
+            // afterward, stays wrong until something else forces a restyle
+            // (reopening the document). Re-measure one runloop tick later,
+            // once layout has actually settled — mirrors the WideTableOverlay
+            // reconciliation below.
+            if imageChanged {
+                let coordinator = context.coordinator
+                DispatchQueue.main.async { [weak textView] in
+                    guard let textView else { return }
+                    let range = NSRange(location: 0, length: (textView.string as NSString).length)
+                    guard range.length > 0 else { return }
+                    coordinator.restyleParagraphs([range], in: textView)
+                }
+            }
         }
         textView.isEditable = isEditable
         textView.isSelectable = true
@@ -562,6 +596,18 @@ public struct NativeTextViewWrapper: NSViewRepresentable {
             }
             return
         }
+        if let pendingTextInsertion {
+            if pendingTextInsertion.documentId == documentId,
+               context.coordinator.lastAppliedTextInsertionID != pendingTextInsertion.id {
+                context.coordinator.applyTextInsertion(pendingTextInsertion, to: textView)
+            }
+            DispatchQueue.main.async {
+                if self.pendingTextInsertion?.id == pendingTextInsertion.id {
+                    self.pendingTextInsertion = nil
+                }
+            }
+            return
+        }
         if context.coordinator.didInitialFormatting
             && context.coordinator.lastSyncedText == text
             && !fontChanged {
@@ -669,6 +715,7 @@ public struct NativeTextViewWrapper: NSViewRepresentable {
         context.coordinator.onInlineSelectionChange = onInlineSelectionChange
         context.coordinator.onInlinePreviewKey = onInlinePreviewKey
         context.coordinator.onCodeBlockSelectionChange = onCodeBlockSelectionChange
+        context.coordinator.onSelectedTextChange = onSelectedTextChange
         context.coordinator.didInitialFormatting = true
     }
 
@@ -691,6 +738,7 @@ public struct NativeTextViewWrapper: NSViewRepresentable {
         coordinator.lastImageFingerprint = configuration.services.images.fingerprint()
         coordinator.lastWikiFingerprint = configuration.services.wikiLinks.fingerprint()
         coordinator.onCodeBlockSelectionChange = onCodeBlockSelectionChange
+        coordinator.onSelectedTextChange = onSelectedTextChange
         coordinator.onInlinePreviewKey = onInlinePreviewKey
         coordinator.userPrefersContinuousSpellChecking = configuration.spellChecking.continuousSpellChecking
         coordinator.userPrefersGrammarChecking = configuration.spellChecking.grammarChecking