feat: create inline (anchored) comments from a text selection

Right-click a selection -> "Comment on Selection..." -> opens the
comments sheet straight into composing, with a removable chip showing
what's being anchored to (clearing it falls back to a plain
document-level comment). Posts via comments.create with anchorText
set to the selection.

Only wired on rendered panes (main reader pane, Split View's preview
pane) - not the raw-markdown pane, since a selection there would
capture literal Markdown syntax as the anchor instead of clean prose.

NSMenuItem has no closure initializer, so this needed a small
target-is-self subclass (ClosureMenuItem) to wire a Swift closure
into onBuildContextMenu's NSMenu without a separate selector per
action.

Also moved the comments sheet's .sheet(...) modifier off the toolbar
badge button (which only exists once the doc already has comments)
onto the view root, since a document with zero comments still needs
to be able to open the sheet to create its first one. Reader now
refetches its own comment list after any create/reply via the sheet's
new onCommentsChanged callback, so a freshly anchored comment's inline
marker appears without reopening the document.

OutlineKit/Sources/OutlineKit/Caching/CachingOutlineAPIClient.swift

@@ -92,6 +92,12 @@ public actor CachingOutlineAPIClient: OutlineAPIClient {
         }
     }
 
+    public func listDrafts(_ request: ListDraftsRequest) async throws -> [OutlineDocument] {
+        try await cachedFetch(key: "documentsDrafts:\(request.offset):\(request.limit)") {
+            try await self.live.listDrafts(request)
+        }
+    }
+
     public func listCollections(offset: Int, limit: Int) async throws -> [OutlineCollection] {
         try await cachedFetch(key: "collections:\(offset):\(limit)") {
             try await self.live.listCollections(offset: offset, limit: limit)
@@ -303,6 +309,34 @@ public actor CachingOutlineAPIClient: OutlineAPIClient {
         try await live.listViews(request)
     }
 
+    public func listComments(_ request: ListCommentsRequest) async throws -> [OutlineComment] {
+        try await live.listComments(request)
+    }
+
+    public func commentInfo(id: String) async throws -> OutlineComment {
+        try await live.commentInfo(id: id)
+    }
+
+    public func createComment(_ request: CreateCommentRequest) async throws -> OutlineComment {
+        try await live.createComment(request)
+    }
+
+    public func resolveComment(id: String) async throws -> OutlineComment {
+        try await live.resolveComment(id: id)
+    }
+
+    public func unresolveComment(id: String) async throws -> OutlineComment {
+        try await live.unresolveComment(id: id)
+    }
+
+    public func addReaction(commentId: String, emoji: String) async throws {
+        try await live.addReaction(commentId: commentId, emoji: emoji)
+    }
+
+    public func removeReaction(commentId: String, emoji: String) async throws {
+        try await live.removeReaction(commentId: commentId, emoji: emoji)
+    }
+
     public func addDocumentUser(_ request: AddDocumentUserRequest) async throws -> OutlineMembership {
         try await live.addDocumentUser(request)
     }
@@ -343,6 +377,10 @@ 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

@@ -13,6 +13,9 @@ public protocol OutlineAPIClient: Sendable {
     func documentsList(_ request: DocumentsListRequest) async throws -> [OutlineDocument]
     /// Documents the current user has recently viewed. Backed by `documents.viewed`.
     func listViewedDocuments(offset: Int, limit: Int) async throws -> [OutlineDocument]
+    /// Draft (unpublished) documents belonging to the current user. Backed
+    /// by `documents.drafts`.
+    func listDrafts(_ request: ListDraftsRequest) 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`.
@@ -48,6 +51,20 @@ public protocol OutlineAPIClient: Sendable {
     /// Historical view records, not live presence. Backed by `views.list`.
     func listViews(_ request: ListViewsRequest) async throws -> [OutlineView]
 
+    /// See `OutlineComment`. `resolve`/`unresolve`/`add_reaction`/
+    /// `remove_reaction` are confirmed real against Outline's own server
+    /// source but aren't in the vendored spec.
+    func listComments(_ request: ListCommentsRequest) async throws -> [OutlineComment]
+    func commentInfo(id: String) async throws -> OutlineComment
+    func createComment(_ request: CreateCommentRequest) async throws -> OutlineComment
+    func resolveComment(id: String) async throws -> OutlineComment
+    func unresolveComment(id: String) async throws -> OutlineComment
+    /// Reaction endpoints return `{success: true}`, not the updated
+    /// comment — callers refetch via `commentInfo` for the fresh
+    /// `reactions` array.
+    func addReaction(commentId: String, emoji: String) async throws
+    func removeReaction(commentId: String, emoji: String) async throws
+
     /// See `OutlineMembership`/`OutlineDocumentMember` — `add` is confirmed
     /// from Outline's official docs, the rest are best-effort.
     func addDocumentUser(_ request: AddDocumentUserRequest) async throws -> OutlineMembership
@@ -75,6 +92,14 @@ 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

@@ -59,6 +59,10 @@ public actor LiveOutlineAPIClient: OutlineAPIClient {
         try await post("documents.viewed", body: PaginationParams(offset: offset, limit: limit))
     }
 
+    public func listDrafts(_ request: ListDraftsRequest) async throws -> [OutlineDocument] {
+        try await post("documents.drafts", body: request)
+    }
+
     public func searchDocuments(_ request: DocumentSearchRequest) async throws -> [OutlineDocumentSearchResult] {
         try await post("documents.search", body: request)
     }
@@ -175,6 +179,34 @@ public actor LiveOutlineAPIClient: OutlineAPIClient {
         try await post("views.list", body: request)
     }
 
+    public func listComments(_ request: ListCommentsRequest) async throws -> [OutlineComment] {
+        try await post("comments.list", body: request)
+    }
+
+    public func commentInfo(id: String) async throws -> OutlineComment {
+        try await post("comments.info", body: StarIDParams(id: id))
+    }
+
+    public func createComment(_ request: CreateCommentRequest) async throws -> OutlineComment {
+        try await post("comments.create", body: request)
+    }
+
+    public func resolveComment(id: String) async throws -> OutlineComment {
+        try await post("comments.resolve", body: StarIDParams(id: id))
+    }
+
+    public func unresolveComment(id: String) async throws -> OutlineComment {
+        try await post("comments.unresolve", body: StarIDParams(id: id))
+    }
+
+    public func addReaction(commentId: String, emoji: String) async throws {
+        try await postForSuccess("comments.add_reaction", body: CommentReactionParams(id: commentId, emoji: emoji))
+    }
+
+    public func removeReaction(commentId: String, emoji: String) async throws {
+        try await postForSuccess("comments.remove_reaction", body: CommentReactionParams(id: commentId, emoji: emoji))
+    }
+
     public func addDocumentUser(_ request: AddDocumentUserRequest) async throws -> OutlineMembership {
         try await post("documents.add_user", body: request)
     }
@@ -278,6 +310,45 @@ 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))
     }
@@ -485,6 +556,11 @@ private struct StarIDParams: Encodable {
     let id: String
 }
 
+private struct CommentReactionParams: Encodable {
+    let id: String
+    let emoji: String
+}
+
 private struct MoveDocumentResponse: Decodable {
     let documents: [OutlineDocument]?
     let collections: [OutlineCollection]?

OutlineKit/Sources/OutlineKit/Models/JSONValue.swift

@@ -0,0 +1,69 @@
+import Foundation
+
+/// Minimal recursive JSON tree for fields the API returns as genuinely
+/// arbitrary/untyped JSON (`type: object` with no fixed schema in the
+/// OpenAPI spec) — currently just `Comment.data`, a ProseMirror document.
+/// Decode-only: nothing in this codebase writes comment bodies back yet.
+public enum JSONValue: Decodable, Sendable {
+    case string(String)
+    case number(Double)
+    case bool(Bool)
+    case object([String: JSONValue])
+    case array([JSONValue])
+    case null
+
+    public init(from decoder: Decoder) throws {
+        let container = try decoder.singleValueContainer()
+        if container.decodeNil() {
+            self = .null
+        } else if let value = try? container.decode(Bool.self) {
+            self = .bool(value)
+        } else if let value = try? container.decode(Double.self) {
+            self = .number(value)
+        } else if let value = try? container.decode(String.self) {
+            self = .string(value)
+        } else if let value = try? container.decode([String: JSONValue].self) {
+            self = .object(value)
+        } else if let value = try? container.decode([JSONValue].self) {
+            self = .array(value)
+        } else {
+            throw DecodingError.dataCorruptedError(in: container, debugDescription: "Unsupported JSON value")
+        }
+    }
+}
+
+extension JSONValue {
+    /// Best-effort plain-text extraction from a ProseMirror-shaped document —
+    /// walks `content` arrays, concatenates `text` node strings, and adds a
+    /// trailing newline after known block-level node types so paragraphs
+    /// don't run together. Good enough for a read-only comment list; not a
+    /// real ProseMirror renderer (no marks, no lists/tables structure).
+    public func plainText() -> String {
+        switch self {
+        case .object(let fields):
+            if case .string(let text)? = fields["text"] {
+                return text
+            }
+            let childText: String
+            if case .array(let items)? = fields["content"] {
+                childText = items.map { $0.plainText() }.joined()
+            } else {
+                childText = ""
+            }
+            if case .string(let type)? = fields["type"], Self.blockTypes.contains(type) {
+                return childText + "\n"
+            }
+            return childText
+        case .array(let items):
+            return items.map { $0.plainText() }.joined()
+        case .string(let value):
+            return value
+        case .number, .bool, .null:
+            return ""
+        }
+    }
+
+    private static let blockTypes: Set<String> = [
+        "paragraph", "heading", "listItem", "blockquote", "codeBlock", "list_item", "code_block"
+    ]
+}

OutlineKit/Sources/OutlineKit/Models/OutlineComment.swift

@@ -0,0 +1,46 @@
+import Foundation
+
+/// A comment (or reply, via `parentCommentId`) on a document. Backed by
+/// `comments.*` — `create`/`info`/`update`/`delete`/`list` are in the
+/// vendored OpenAPI spec; `resolve`/`unresolve`/`add_reaction`/
+/// `remove_reaction` are not (confirmed against Outline's own server
+/// source instead — same "spec mirror is incomplete" lesson as
+/// `OutlinePin`). `data` is the comment body as a ProseMirror document,
+/// not plain text — see `JSONValue.plainText()`.
+public struct OutlineComment: Decodable, Identifiable, Sendable {
+    public let id: String
+    public let data: JSONValue
+    public let documentId: String
+    public let parentCommentId: String?
+    public let createdAt: Date
+    public let createdBy: OutlineUser?
+    public let updatedAt: Date?
+    public let resolvedAt: Date?
+    public let resolvedBy: OutlineUser?
+    public let reactions: [ReactionSummary]
+    /// The document text this comment is anchored to — only populated when
+    /// the request set `includeAnchorText: true`; `nil` for a document-level
+    /// (non-anchored) comment either way. No prefix/suffix comes back on
+    /// read (only accepted as create-time disambiguation input), so
+    /// re-finding this text in the rendered document is inherently
+    /// best-effort — first occurrence wins, same as Outline's own create
+    /// behavior when nothing else disambiguates.
+    public let anchorText: String?
+
+    public var isResolved: Bool { resolvedAt != nil }
+    public var bodyText: String {
+        data.plainText().trimmingCharacters(in: .whitespacesAndNewlines)
+    }
+}
+
+/// One emoji's worth of reactions on a comment — grouped by emoji server-side
+/// (`ReactionSummary` in Outline's own source), not one object per reaction.
+public struct ReactionSummary: Codable, Sendable, Equatable {
+    public let emoji: String
+    public let userIds: [String]
+
+    public init(emoji: String, userIds: [String]) {
+        self.emoji = emoji
+        self.userIds = userIds
+    }
+}

OutlineKit/Sources/OutlineKit/Requests/CreateCommentRequest.swift

@@ -0,0 +1,26 @@
+import Foundation
+
+/// `parentCommentId: nil` creates a document-level (top-level) comment;
+/// non-nil creates a reply (Outline supports one level of nesting — a
+/// reply's own `parentCommentId` should always be a top-level comment's
+/// id, never another reply's). `anchorText` creates an inline (anchored)
+/// comment instead of a document-level one — the first occurrence of that
+/// exact substring in the document's plain text is used, same as Outline's
+/// own web editor; `anchorPrefix`/`anchorSuffix` aren't sent (this app has
+/// no UI for choosing between multiple identical occurrences). `text` is
+/// the documented markdown convenience field for `data` (a ProseMirror
+/// document) — simplest path for plain-text comment bodies, no need to
+/// construct ProseMirror JSON by hand.
+public struct CreateCommentRequest: Encodable, Sendable {
+    public let documentId: String
+    public let parentCommentId: String?
+    public let text: String
+    public let anchorText: String?
+
+    public init(documentId: String, parentCommentId: String? = nil, text: String, anchorText: String? = nil) {
+        self.documentId = documentId
+        self.parentCommentId = parentCommentId
+        self.text = text
+        self.anchorText = anchorText
+    }
+}

OutlineKit/Sources/OutlineKit/Requests/CreateDocumentRequest.swift

@@ -3,14 +3,16 @@ import Foundation
 public struct CreateDocumentRequest: Codable, Sendable {
     public let title: String
     public let text: String
-    public let collectionId: String
+    /// `nil` (with `parentDocumentId` also `nil`) creates a draft — Outline
+    /// requires one of the two to publish at all, regardless of `publish`.
+    public let collectionId: String?
     public let parentDocumentId: String?
     public let publish: Bool
 
     public init(
         title: String,
         text: String,
-        collectionId: String,
+        collectionId: String? = nil,
         parentDocumentId: String? = nil,
         publish: Bool = true
     ) {

OutlineKit/Sources/OutlineKit/Requests/ListCommentsRequest.swift

@@ -0,0 +1,18 @@
+import Foundation
+
+public struct ListCommentsRequest: Encodable, Sendable {
+    public let documentId: String
+    public let offset: Int
+    public let limit: Int
+    /// Include each anchored comment's `anchorText` (the document text it's
+    /// attached to) in the response. Off by default — it's extra payload
+    /// only needed when actually positioning inline markers.
+    public let includeAnchorText: Bool
+
+    public init(documentId: String, offset: Int = 0, limit: Int = 100, includeAnchorText: Bool = false) {
+        self.documentId = documentId
+        self.offset = offset
+        self.limit = limit
+        self.includeAnchorText = includeAnchorText
+    }
+}

OutlineKit/Sources/OutlineKit/Requests/ListDraftsRequest.swift

@@ -0,0 +1,11 @@
+import Foundation
+
+public struct ListDraftsRequest: Encodable, Sendable {
+    public let offset: Int
+    public let limit: Int
+
+    public init(offset: Int = 0, limit: Int = 25) {
+        self.offset = offset
+        self.limit = limit
+    }
+}

OutlineKit/Sources/OutlineKit/Requests/UpdateDocumentRequest.swift

@@ -7,6 +7,13 @@ public struct UpdateDocumentRequest: Codable, Sendable {
     public let append: Bool?
     public let fullWidth: Bool?
     public let insightsEnabled: Bool?
+    /// Moves the document to this collection. Combined with `publish: true`,
+    /// this is how a draft (no `collectionId`, or one it just hasn't left
+    /// yet) gets published into a specific collection in one call.
+    public let collectionId: String?
+    /// Publishes a draft, making it visible to other workspace members.
+    /// Documented as a no-op if the document is already published.
+    public let publish: Bool?
 
     public init(
         id: String,
@@ -14,7 +21,9 @@ public struct UpdateDocumentRequest: Codable, Sendable {
         text: String? = nil,
         append: Bool? = nil,
         fullWidth: Bool? = nil,
-        insightsEnabled: Bool? = nil
+        insightsEnabled: Bool? = nil,
+        collectionId: String? = nil,
+        publish: Bool? = nil
     ) {
         self.id = id
         self.title = title
@@ -22,5 +31,7 @@ public struct UpdateDocumentRequest: Codable, Sendable {
         self.append = append
         self.fullWidth = fullWidth
         self.insightsEnabled = insightsEnabled
+        self.collectionId = collectionId
+        self.publish = publish
     }
 }

OutlineKit/Tests/OutlineKitTests/CachingOutlineAPIClientTests.swift

@@ -29,6 +29,7 @@ private final class StubOutlineAPIClient: OutlineAPIClient, @unchecked Sendable
 
     func documentsList(_ request: DocumentsListRequest) async throws -> [OutlineDocument] { throw NotStubbed() }
     func listViewedDocuments(offset: Int, limit: Int) async throws -> [OutlineDocument] { throw NotStubbed() }
+    func listDrafts(_ request: ListDraftsRequest) async throws -> [OutlineDocument] { throw NotStubbed() }
     func searchDocuments(_ request: DocumentSearchRequest) async throws -> [OutlineDocumentSearchResult] { throw NotStubbed() }
     func searchDocumentTitles(_ request: DocumentSearchTitlesRequest) async throws -> [OutlineDocument] { throw NotStubbed() }
     func createDocument(_ request: CreateDocumentRequest) async throws -> OutlineDocument {
@@ -71,6 +72,13 @@ private final class StubOutlineAPIClient: OutlineAPIClient, @unchecked Sendable
     func listSubscriptions(_ request: ListSubscriptionsRequest) async throws -> [OutlineSubscription] { throw NotStubbed() }
     func deleteSubscription(id: String) async throws { throw NotStubbed() }
     func listViews(_ request: ListViewsRequest) async throws -> [OutlineView] { throw NotStubbed() }
+    func listComments(_ request: ListCommentsRequest) async throws -> [OutlineComment] { throw NotStubbed() }
+    func commentInfo(id: String) async throws -> OutlineComment { throw NotStubbed() }
+    func createComment(_ request: CreateCommentRequest) async throws -> OutlineComment { throw NotStubbed() }
+    func resolveComment(id: String) async throws -> OutlineComment { throw NotStubbed() }
+    func unresolveComment(id: String) async throws -> OutlineComment { throw NotStubbed() }
+    func addReaction(commentId: String, emoji: String) async throws { throw NotStubbed() }
+    func removeReaction(commentId: String, emoji: String) async throws { throw NotStubbed() }
     func addDocumentUser(_ request: AddDocumentUserRequest) async throws -> OutlineMembership { throw NotStubbed() }
     func removeDocumentUser(_ request: RemoveDocumentUserRequest) async throws { throw NotStubbed() }
     func documentUsers(_ request: ListDocumentUsersRequest) async throws -> [OutlineDocumentMember] { throw NotStubbed() }
@@ -91,6 +99,7 @@ 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() }

OutlineKit/Tests/OutlineKitTests/LiveOutlineAPIClientTests.swift

@@ -846,6 +846,137 @@ final class LiveOutlineAPIClientTests: XCTestCase {
         XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/views.list")
     }
 
+    func testListCommentsDecodesCommentsAndExtractsPlainTextFromProseMirrorData() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": [
+                {
+                    "id": "comment-1",
+                    "documentId": "doc-1",
+                    "parentCommentId": null,
+                    "createdAt": "2026-01-01T00:00:00.000Z",
+                    "createdBy": { "id": "user-1", "name": "Jane Doe" },
+                    "updatedAt": "2026-01-01T00:00:00.000Z",
+                    "resolvedAt": null,
+                    "resolvedBy": null,
+                    "reactions": [
+                        { "emoji": "\u{1F44D}", "userIds": ["user-2", "user-3"] }
+                    ],
+                    "data": {
+                        "type": "doc",
+                        "content": [
+                            {
+                                "type": "paragraph",
+                                "content": [
+                                    { "type": "text", "text": "Sounds great" }
+                                ]
+                            }
+                        ]
+                    }
+                }
+            ]
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let comments = try await client.listComments(ListCommentsRequest(documentId: "doc-1"))
+
+        XCTAssertEqual(comments.first?.id, "comment-1")
+        XCTAssertEqual(comments.first?.bodyText, "Sounds great")
+        XCTAssertFalse(comments.first?.isResolved ?? true)
+        XCTAssertEqual(comments.first?.reactions.first?.emoji, "\u{1F44D}")
+        XCTAssertEqual(comments.first?.reactions.first?.userIds, ["user-2", "user-3"])
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/comments.list")
+    }
+
+    func testResolveCommentDecodesResolvedComment() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "comment-1",
+                "documentId": "doc-1",
+                "parentCommentId": null,
+                "createdAt": "2026-01-01T00:00:00.000Z",
+                "createdBy": { "id": "user-1", "name": "Jane Doe" },
+                "updatedAt": "2026-01-01T00:00:00.000Z",
+                "resolvedAt": "2026-01-02T00:00:00.000Z",
+                "resolvedBy": { "id": "user-2", "name": "John Roe" },
+                "reactions": [],
+                "data": { "type": "doc", "content": [] }
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let comment = try await client.resolveComment(id: "comment-1")
+
+        XCTAssertTrue(comment.isResolved)
+        XCTAssertEqual(comment.resolvedBy?.name, "John Roe")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/comments.resolve")
+    }
+
+    func testCreateCommentSendsParentCommentIdForAReply() async throws {
+        let httpClient = MockHTTPClient()
+        httpClient.responseData = """
+        {
+            "data": {
+                "id": "comment-2",
+                "documentId": "doc-1",
+                "parentCommentId": "comment-1",
+                "createdAt": "2026-01-01T00:00:00.000Z",
+                "createdBy": { "id": "user-1", "name": "Jane Doe" },
+                "updatedAt": "2026-01-01T00:00:00.000Z",
+                "resolvedAt": null,
+                "resolvedBy": null,
+                "reactions": [],
+                "data": { "type": "doc", "content": [] }
+            }
+        }
+        """.data(using: .utf8)!
+
+        let client = LiveOutlineAPIClient(
+            configuration: OutlineConfiguration(baseURL: URL(string: "https://outline.example.com")!),
+            tokenStore: StaticTokenStore(),
+            httpClient: httpClient
+        )
+
+        let reply = try await client.createComment(
+            CreateCommentRequest(documentId: "doc-1", parentCommentId: "comment-1", text: "Agreed")
+        )
+
+        XCTAssertEqual(reply.parentCommentId, "comment-1")
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/comments.create")
+    }
+
+    func testAddReactionPostsIdAndEmoji() 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.addReaction(commentId: "comment-1", emoji: "\u{1F44D}")
+
+        XCTAssertEqual(httpClient.lastRequest?.url?.path, "/api/comments.add_reaction")
+    }
+
     func testCreatePinDecodesPin() async throws {
         let httpClient = MockHTTPClient()
         httpClient.responseData = """

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/ContentView_macOS.swift

@@ -445,6 +445,13 @@ struct ContentView_macOS: View {
                             if !documentPath.isEmpty {
                                 documentPath.removeLast()
                             }
+                            // Delete/Archive/Unpublish/Move all change what
+                            // should show in the sidebar tree — this only
+                            // popped the reader before, leaving the sidebar
+                            // showing the document until some unrelated
+                            // trigger (the 45s poll, navigating away and
+                            // back) happened to refresh it.
+                            documentsChangedToken += 1
                         },
                         onDocumentCreated: { documentsChangedToken += 1 }
                     )

Outpost/Features/Collections/DocumentCommentsSheet.swift

@@ -0,0 +1,425 @@
+#if os(macOS)
+import SwiftUI
+import OutlineKit
+
+/// Document-level and anchored comments + single-level replies + emoji
+/// reactions + resolve/unresolve. Composing new comments/replies is still
+/// plain text only (no bold/italic/lists/etc.) — sent through the `text`
+/// (markdown) convenience field, not a hand-built ProseMirror `data`
+/// document.
+@MainActor
+struct DocumentCommentsSheet: View {
+    @Environment(\.dismiss) private var dismiss
+
+    let apiClient: OutlineAPIClient
+    let document: OutlineDocument
+    /// Set when opened by tapping an inline anchor marker — scrolls to and
+    /// briefly highlights that comment/reply. `nil` opens unfocused (the
+    /// plain toolbar marker).
+    var focusedCommentId: String? = nil
+    /// Set when opened via "Comment on Selection…" from the editor's
+    /// right-click menu — the selected text to anchor a NEW comment to.
+    /// The first occurrence of this exact substring in the document is
+    /// what the server (and later, this app's own inline marker) anchors
+    /// to; no prefix/suffix disambiguation UI for multiple identical
+    /// occurrences.
+    var pendingAnchorText: String? = nil
+    /// Called after any successful create/reply/resolve/reaction — lets the
+    /// reader refresh its own lightweight copy (inline anchor markers, the
+    /// toolbar badge count) without waiting for the document to be reopened.
+    var onCommentsChanged: (() -> Void)? = nil
+
+    /// A small curated set rather than the full system emoji picker — quick
+    /// taps for the common reactions, matching how most chat apps default.
+    private static let quickReactions = ["👍", "❤️", "😂", "🎉", "😮", "😢"]
+
+    @State private var comments: [OutlineComment] = []
+    @State private var isLoading = false
+    @State private var errorMessage: String?
+    @State private var actionErrorMessage: String?
+    @State private var currentUserId: String?
+
+    @State private var newCommentText = ""
+    @State private var isPostingNewComment = false
+    /// Mutable mirror of `pendingAnchorText` — lets the user clear it (fall
+    /// back to a plain document-level comment) without touching the init
+    /// param itself.
+    @State private var composingAnchorText: String?
+
+    @State private var replyingToThreadId: String?
+    @State private var replyText = ""
+    @State private var isPostingReply = false
+
+    @State private var resolvingCommentIds: Set<String> = []
+    @State private var reactingCommentIds: Set<String> = []
+    @State private var reactionPickerCommentId: String?
+
+    private struct CommentThread: Identifiable {
+        let top: OutlineComment
+        let replies: [OutlineComment]
+        var id: String { top.id }
+    }
+
+    private var threads: [CommentThread] {
+        let topLevel = comments.filter { $0.parentCommentId == nil }.sorted { $0.createdAt < $1.createdAt }
+        return topLevel.map { top in
+            let replies = comments
+                .filter { $0.parentCommentId == top.id }
+                .sorted { $0.createdAt < $1.createdAt }
+            return CommentThread(top: top, replies: replies)
+        }
+    }
+
+    var body: some View {
+        VStack(alignment: .leading, spacing: 0) {
+            HStack {
+                Text("Comments")
+                    .font(.headline)
+                Spacer()
+                Button("Done") { dismiss() }
+            }
+            .padding()
+
+            Divider()
+
+            Group {
+                if isLoading && comments.isEmpty {
+                    ProgressView().frame(maxWidth: .infinity, maxHeight: .infinity)
+                } else if let errorMessage {
+                    ContentUnavailableView {
+                        Label("Couldn't Load Comments", systemImage: "exclamationmark.triangle")
+                    } description: {
+                        Text(errorMessage)
+                    } actions: {
+                        Button("Retry") { Task { await load() } }
+                    }
+                } else if threads.isEmpty {
+                    ContentUnavailableView {
+                        Label("No Comments", systemImage: "bubble.left.and.bubble.right")
+                    } description: {
+                        Text("This document has no comments yet.")
+                    }
+                } else {
+                    ScrollViewReader { proxy in
+                        List(threads) { thread in
+                            threadSection(thread)
+                        }
+                        .task {
+                            guard let focusedCommentId else { return }
+                            // The list needs a beat to lay out before a
+                            // scrollTo lands correctly on first appear.
+                            try? await Task.sleep(for: .milliseconds(50))
+                            withAnimation {
+                                proxy.scrollTo(focusedCommentId, anchor: .center)
+                            }
+                        }
+                    }
+                }
+            }
+            .frame(maxWidth: .infinity, maxHeight: .infinity)
+
+            Divider()
+            newCommentComposer
+        }
+        .frame(width: 480, height: 560)
+        .task { await load() }
+        .task { currentUserId = try? await apiClient.currentUser().id }
+        .task { composingAnchorText = pendingAnchorText }
+        .alert("Couldn't Complete Action", isPresented: .constant(actionErrorMessage != nil)) {
+            Button("OK") { actionErrorMessage = nil }
+        } message: {
+            Text(actionErrorMessage ?? "")
+        }
+    }
+
+    // MARK: - Thread
+
+    private func threadSection(_ thread: CommentThread) -> some View {
+        VStack(alignment: .leading, spacing: 8) {
+            commentRow(thread.top, isReply: false)
+
+            ForEach(thread.replies) { reply in
+                commentRow(reply, isReply: true)
+                    .padding(.leading, 20)
+            }
+
+            if replyingToThreadId == thread.id {
+                replyComposer(for: thread)
+                    .padding(.leading, 20)
+            } else {
+                Button("Reply") {
+                    replyingToThreadId = thread.id
+                    replyText = ""
+                }
+                .buttonStyle(.plain)
+                .font(.caption.weight(.semibold))
+                .foregroundStyle(.blue)
+                .padding(.leading, 20)
+            }
+        }
+        .padding(.vertical, 6)
+    }
+
+    private func commentRow(_ comment: OutlineComment, isReply: Bool) -> some View {
+        VStack(alignment: .leading, spacing: 6) {
+            HStack(spacing: 6) {
+                Text(comment.createdBy?.name ?? "Unknown")
+                    .font(.callout.weight(.semibold))
+                Spacer()
+                Text(comment.createdAt, format: .relative(presentation: .named))
+                    .font(.caption)
+                    .foregroundStyle(.secondary)
+            }
+
+            Text(comment.bodyText.isEmpty ? "(empty)" : comment.bodyText)
+                .font(.callout)
+                .foregroundStyle(comment.bodyText.isEmpty ? .secondary : .primary)
+
+            if !comment.reactions.isEmpty {
+                reactionChips(comment)
+            }
+
+            HStack(spacing: 12) {
+                Button {
+                    reactionPickerCommentId = comment.id
+                } label: {
+                    Image(systemName: "face.smiling")
+                }
+                .buttonStyle(.plain)
+                .foregroundStyle(.secondary)
+                .popover(isPresented: Binding(
+                    get: { reactionPickerCommentId == comment.id },
+                    set: { if !$0 { reactionPickerCommentId = nil } }
+                )) {
+                    quickReactionPicker(comment)
+                }
+
+                if !isReply {
+                    if comment.isResolved {
+                        Label("Resolved", systemImage: "checkmark.circle.fill")
+                            .font(.caption)
+                            .foregroundStyle(.green)
+                    }
+                    Spacer()
+                    if resolvingCommentIds.contains(comment.id) {
+                        ProgressView().controlSize(.small)
+                    } else {
+                        Button(comment.isResolved ? "Unresolve" : "Resolve") {
+                            Task { await toggleResolved(comment) }
+                        }
+                        .buttonStyle(.plain)
+                        .font(.caption.weight(.semibold))
+                        .foregroundStyle(.blue)
+                    }
+                } else {
+                    Spacer()
+                }
+            }
+        }
+        .padding(6)
+        .background(
+            comment.id == focusedCommentId ? Color.accentColor.opacity(0.12) : Color.clear,
+            in: RoundedRectangle(cornerRadius: 6)
+        )
+        .id(comment.id)
+    }
+
+    private func reactionChips(_ comment: OutlineComment) -> some View {
+        HStack(spacing: 4) {
+            ForEach(comment.reactions, id: \.emoji) { reaction in
+                let mine = currentUserId.map(reaction.userIds.contains) ?? false
+                Button {
+                    Task { await toggleReaction(comment, emoji: reaction.emoji, currentlyReacted: mine) }
+                } label: {
+                    Text("\(reaction.emoji) \(reaction.userIds.count)")
+                        .font(.caption)
+                        .padding(.horizontal, 6)
+                        .padding(.vertical, 2)
+                        .background(mine ? Color.accentColor.opacity(0.2) : Color.gray.opacity(0.15), in: Capsule())
+                }
+                .buttonStyle(.plain)
+                .disabled(reactingCommentIds.contains(comment.id))
+            }
+        }
+    }
+
+    private func quickReactionPicker(_ comment: OutlineComment) -> some View {
+        HStack(spacing: 8) {
+            ForEach(Self.quickReactions, id: \.self) { emoji in
+                let mine = currentUserId.map { userId in
+                    comment.reactions.first { $0.emoji == emoji }?.userIds.contains(userId) ?? false
+                } ?? false
+                Button {
+                    reactionPickerCommentId = nil
+                    Task { await toggleReaction(comment, emoji: emoji, currentlyReacted: mine) }
+                } label: {
+                    Text(emoji)
+                        .font(.title2)
+                        .opacity(mine ? 1 : 0.5)
+                }
+                .buttonStyle(.plain)
+            }
+        }
+        .padding(10)
+    }
+
+    // MARK: - Composers
+
+    private var newCommentComposer: some View {
+        VStack(alignment: .leading, spacing: 6) {
+            if let composingAnchorText {
+                HStack(spacing: 6) {
+                    Image(systemName: "text.quote")
+                        .foregroundStyle(.blue)
+                    Text(composingAnchorText)
+                        .font(.caption)
+                        .foregroundStyle(.secondary)
+                        .lineLimit(1)
+                        .truncationMode(.tail)
+                    Spacer()
+                    Button {
+                        self.composingAnchorText = nil
+                    } label: {
+                        Image(systemName: "xmark.circle.fill")
+                    }
+                    .buttonStyle(.plain)
+                    .foregroundStyle(.secondary)
+                    .help("Remove — this will post as a document-level comment instead")
+                }
+                .padding(.horizontal, 6)
+                .padding(.vertical, 4)
+                .background(Color.blue.opacity(0.1), in: RoundedRectangle(cornerRadius: 6))
+            }
+            HStack(alignment: .bottom, spacing: 8) {
+                TextField(
+                    composingAnchorText == nil ? "Add a comment…" : "Comment on this text…",
+                    text: $newCommentText,
+                    axis: .vertical
+                )
+                .textFieldStyle(.roundedBorder)
+                .lineLimit(1...4)
+                .onSubmit { Task { await postNewComment() } }
+                if isPostingNewComment {
+                    ProgressView().controlSize(.small)
+                } else {
+                    Button("Post") {
+                        Task { await postNewComment() }
+                    }
+                    .disabled(newCommentText.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty)
+                }
+            }
+        }
+        .padding()
+    }
+
+    private func replyComposer(for thread: CommentThread) -> some View {
+        HStack(alignment: .bottom, spacing: 8) {
+            TextField("Reply…", text: $replyText, axis: .vertical)
+                .textFieldStyle(.roundedBorder)
+                .lineLimit(1...4)
+                .onSubmit { Task { await postReply(to: thread) } }
+            if isPostingReply {
+                ProgressView().controlSize(.small)
+            } else {
+                Button("Send") {
+                    Task { await postReply(to: thread) }
+                }
+                .disabled(replyText.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty)
+                Button("Cancel") {
+                    replyingToThreadId = nil
+                    replyText = ""
+                }
+                .buttonStyle(.plain)
+                .foregroundStyle(.secondary)
+            }
+        }
+    }
+
+    // MARK: - Actions
+
+    private func load() async {
+        isLoading = true
+        defer { isLoading = false }
+        do {
+            comments = try await apiClient.listComments(ListCommentsRequest(documentId: document.id))
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Couldn't load comments for this document.")
+        }
+    }
+
+    private func postNewComment() async {
+        let text = newCommentText.trimmingCharacters(in: .whitespacesAndNewlines)
+        guard !text.isEmpty else { return }
+        isPostingNewComment = true
+        defer { isPostingNewComment = false }
+        do {
+            let created = try await apiClient.createComment(
+                CreateCommentRequest(documentId: document.id, text: text, anchorText: composingAnchorText)
+            )
+            comments.append(created)
+            composingAnchorText = nil
+            newCommentText = ""
+            onCommentsChanged?()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't post this comment.")
+        }
+    }
+
+    private func postReply(to thread: CommentThread) async {
+        let text = replyText.trimmingCharacters(in: .whitespacesAndNewlines)
+        guard !text.isEmpty else { return }
+        isPostingReply = true
+        defer { isPostingReply = false }
+        do {
+            let created = try await apiClient.createComment(
+                CreateCommentRequest(documentId: document.id, parentCommentId: thread.id, text: text)
+            )
+            comments.append(created)
+            replyText = ""
+            replyingToThreadId = nil
+            onCommentsChanged?()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't post this reply.")
+        }
+    }
+
+    private func toggleResolved(_ comment: OutlineComment) async {
+        resolvingCommentIds.insert(comment.id)
+        defer { resolvingCommentIds.remove(comment.id) }
+        do {
+            let updated = comment.isResolved
+                ? try await apiClient.unresolveComment(id: comment.id)
+                : try await apiClient.resolveComment(id: comment.id)
+            replace(updated)
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't update this comment.")
+        }
+    }
+
+    /// Reaction endpoints return `{success: true}`, not the updated comment
+    /// (see `OutlineAPIClient.addReaction`) — refetch via `commentInfo` for
+    /// the real post-toggle `reactions` array instead of guessing the merge
+    /// locally (another user reacting concurrently would make a guess wrong).
+    private func toggleReaction(_ comment: OutlineComment, emoji: String, currentlyReacted: Bool) async {
+        reactingCommentIds.insert(comment.id)
+        defer { reactingCommentIds.remove(comment.id) }
+        do {
+            if currentlyReacted {
+                try await apiClient.removeReaction(commentId: comment.id, emoji: emoji)
+            } else {
+                try await apiClient.addReaction(commentId: comment.id, emoji: emoji)
+            }
+            let refreshed = try await apiClient.commentInfo(id: comment.id)
+            replace(refreshed)
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't update that reaction.")
+        }
+    }
+
+    private func replace(_ updated: OutlineComment) {
+        if let index = comments.firstIndex(where: { $0.id == updated.id }) {
+            comments[index] = updated
+        }
+    }
+}
+#endif

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
@@ -66,16 +83,62 @@ struct DocumentReaderView: View {
     let onDocumentCreated: () -> Void
 
     @State private var isShowingUnpublishConfirmation = false
+    @State private var isShowingPublishSheet = 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 isShowingCommentsSheet = false
+    /// Fetched once on load, purely to drive the toolbar marker/badge and
+    /// the inline anchor bars below — the sheet itself fetches its own copy
+    /// independently (see `DocumentCommentsSheet`), same as every other
+    /// self-contained sheet in this file.
+    @State private var loadedComments: [OutlineComment] = []
+    /// Comment id to scroll/focus to when the sheet opens — set when an
+    /// inline anchor bar is tapped, `nil` for the plain toolbar marker.
+    @State private var focusedCommentId: String?
+    /// Resolved on-screen positions for each anchored comment's text, from
+    /// `NativeTextViewWrapper.onCommentAnchorRectsChange`.
+    @State private var commentAnchorRects: [CommentAnchorRect] = []
+    /// Set from "Comment on Selection…" in the editor's right-click menu —
+    /// the sheet opens straight into composing a new anchored comment.
+    @State private var pendingCommentAnchorText: String?
+
+    private var commentCount: Int? {
+        loadedComments.isEmpty ? nil : loadedComments.count
+    }
+    private var commentAnchorQueries: [CommentAnchorQuery] {
+        loadedComments.compactMap { comment in
+            guard let anchorText = comment.anchorText, !anchorText.isEmpty else { return nil }
+            return CommentAnchorQuery(id: comment.id, anchorText: anchorText)
+        }
+    }
     @State private var isShowingPresentSheet = false
     @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 +163,7 @@ 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 +221,44 @@ struct DocumentReaderView: View {
                     DocumentShareSheet(apiClient: apiClient, documentId: viewModel.documentId)
                 }
 
+                // Toolbar marker — only shows once there's actually
+                // something to point at. Anchored comments additionally get
+                // an inline vertical bar next to their text (see
+                // `commentAnchorMarkers`/`onCommentAnchorRectsChange`
+                // below) — this button opens the sheet unfocused, showing
+                // every comment/thread.
+                if let commentCount, commentCount > 0 {
+                    Button {
+                        focusedCommentId = nil
+                        pendingCommentAnchorText = nil
+                        isShowingCommentsSheet = true
+                    } label: {
+                        Image(systemName: "bubble.left.and.bubble.right")
+                    }
+                    .help("\(commentCount) Comment\(commentCount == 1 ? "" : "s")")
+                    .disabled(!isEffectivelyOnline)
+                    .overlay(alignment: .topTrailing) {
+                        Text(commentCount > 10 ? "10+" : "\(commentCount)")
+                            .font(.system(size: 8, weight: .bold))
+                            .foregroundStyle(.white)
+                            .padding(2)
+                            .frame(minWidth: 12, minHeight: 12)
+                            .background(.blue, in: Circle())
+                            .offset(x: 0, y: -1)
+                    }
+                }
+
+                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 +299,12 @@ 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.
@@ -215,6 +323,11 @@ struct DocumentReaderView: View {
         .task {
             await viewModel.loadInsightsEnabledState()
         }
+        .task {
+            loadedComments = (try? await apiClient.listComments(
+                ListCommentsRequest(documentId: viewModel.documentId, includeAnchorText: true)
+            )) ?? []
+        }
         .task {
             while !Task.isCancelled {
                 await viewModel.loadViewers()
@@ -262,6 +375,36 @@ struct DocumentReaderView: View {
         } message: {
             Text(actionErrorMessage ?? "")
         }
+        .sheet(isPresented: $isShowingCommentsSheet) {
+            DocumentCommentsSheet(
+                apiClient: apiClient,
+                document: document,
+                focusedCommentId: focusedCommentId,
+                pendingAnchorText: pendingCommentAnchorText,
+                onCommentsChanged: {
+                    Task {
+                        loadedComments = (try? await apiClient.listComments(
+                            ListCommentsRequest(documentId: viewModel.documentId, includeAnchorText: true)
+                        )) ?? loadedComments
+                    }
+                }
+            )
+        }
+        .sheet(isPresented: $isShowingPublishSheet) {
+            PublishDocumentSheet(apiClient: apiClient, document: document) {
+                // Stays in the reader — unlike Move/Unpublish, publishing
+                // doesn't make the document any less visible from here, so
+                // there's no reason to pop back like onDeleted() does
+                // elsewhere. Refresh from the server rather than guessing
+                // the new collectionId locally (moveDocument may have run
+                // as a second step inside the sheet).
+                await viewModel.loadFullContent()
+                // The doc previously had no collectionId (or a different
+                // one) — the sidebar tree for its new collection needs to
+                // know it exists now, same signal "New Document" sends.
+                onDocumentCreated()
+            }
+        }
         .sheet(isPresented: $isShowingMoveSheet) {
             MoveDocumentSheet(apiClient: apiClient, document: document) {
                 onDeleted()
@@ -285,6 +428,59 @@ struct DocumentReaderView: View {
                 onOpenChild(child)
             }
         }
+        .modifier(ImagePlaygroundPresenter(
+            isPresented: $isShowingImagePlayground,
+            seedText: imagePlaygroundSeedText,
+            seedTitle: viewModel.title.isEmpty ? "Untitled" : viewModel.title,
+            onCompletion: { url in handleGeneratedImage(url) }
+        ))
+    }
+
+    /// Adds "Comment on Selection…" to the right-click menu when there's an
+    /// actual (non-empty) selection to anchor to — `currentSelectedText` is
+    /// kept live by `onSelectedTextChange` on the same pane. Inserted at the
+    /// top since it's the primary reason to right-click selected text here,
+    /// matching Outline's own web editor surfacing comment as the first
+    /// selection action.
+    private func addCommentMenuItem(to menu: NSMenu) -> NSMenu {
+        guard let selection = currentSelectedText, !selection.isEmpty else { return menu }
+        let item = ClosureMenuItem(title: "Comment on Selection…") {
+            pendingCommentAnchorText = selection
+            focusedCommentId = nil
+            isShowingCommentsSheet = true
+        }
+        menu.insertItem(item, at: 0)
+        menu.insertItem(.separator(), at: 1)
+        return menu
+    }
+
+    /// 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 +546,9 @@ 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,
@@ -360,13 +557,24 @@ struct DocumentReaderView: View {
                             ),
                             documentId: viewModel.documentId,
                             isEditable: viewModel.isEffectivelyEditable,
-                            onCodeBlockSelectionChange: { readerCodeBlocks = $0 }
+                            onBuildContextMenu: { menu, _ in addCommentMenuItem(to: menu) },
+                            onCodeBlockSelectionChange: { readerCodeBlocks = $0 },
+                            onSelectedTextChange: { currentSelectedText = $0 },
+                            commentAnchorQueries: commentAnchorQueries,
+                            onCommentAnchorRectsChange: { commentAnchorRects = $0 }
                         )
                         if showCodeBlockLineNumbers {
                             ForEach(readerCodeBlocks) { selection in
                                 CodeBlockLineNumberGutter(selection: selection, gutterWidth: Self.lineNumberGutterWidth)
                             }
                         }
+                        ForEach(commentAnchorRects) { anchor in
+                            CommentAnchorMarker(rect: anchor.rect) {
+                                focusedCommentId = anchor.id
+                                pendingCommentAnchorText = nil
+                                isShowingCommentsSheet = true
+                            }
+                        }
                     }
                 }
             }
@@ -394,11 +602,13 @@ struct DocumentReaderView: View {
         }
     }
 
-    /// Left is a plain, unrendered raw-text editor (deliberately not
+    /// Left is the literal Markdown source in `rawSourceMode` (no syntax
-    /// `NativeTextViewWrapper` — just the literal Markdown source); right
+    /// hiding/styling, but still the real engine — needed so selection
-    /// is the same rich rendering used everywhere else in the app,
+    /// tracking and caret-position insertion, e.g. from the Image Playground
-    /// read-only, bound to the same `viewModel.text` so it updates live as
+    /// button, work here the same as everywhere else); right is the same
-    /// the left side is typed into.
+    /// 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
@@ -408,30 +618,47 @@ struct DocumentReaderView: View {
     /// follow-up, not attempted here.
     private var splitEditorView: some View {
         HSplitView {
-            TextEditor(text: $viewModel.text)
+            NativeTextViewWrapper(
-                .font(.system(.body, design: .monospaced))
+                text: $viewModel.text,
-                .scrollContentBackground(.hidden)
+                pendingTextInsertion: $pendingTextInsertion,
-                .padding(8)
+                configuration: .init(rawSourceMode: true),
-                .frame(minWidth: 300, maxWidth: .infinity, maxHeight: .infinity)
+                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 }
+                        onBuildContextMenu: { menu, _ in addCommentMenuItem(to: menu) },
+                        onCodeBlockSelectionChange: { previewCodeBlocks = $0 },
+                        onSelectedTextChange: { currentSelectedText = $0 },
+                        commentAnchorQueries: commentAnchorQueries,
+                        onCommentAnchorRectsChange: { commentAnchorRects = $0 }
                     )
                     if showCodeBlockLineNumbers {
                         ForEach(previewCodeBlocks) { selection in
                             CodeBlockLineNumberGutter(selection: selection, gutterWidth: Self.lineNumberGutterWidth)
                         }
                     }
+                    ForEach(commentAnchorRects) { anchor in
+                        CommentAnchorMarker(rect: anchor.rect) {
+                            focusedCommentId = anchor.id
+                            pendingCommentAnchorText = nil
+                            isShowingCommentsSheet = true
+                        }
+                    }
                 }
                 .padding(8)
                 .frame(maxWidth: .infinity, alignment: .topLeading)
@@ -476,10 +703,17 @@ struct DocumentReaderView: View {
             Task { await duplicate() }
         }
         .disabled(!isEffectivelyOnline)
-        Button("Unpublish") {
+        if viewModel.publishedAt == nil {
-            isShowingUnpublishConfirmation = true
+            Button("Publish…") {
+                isShowingPublishSheet = true
+            }
+            .disabled(!isEffectivelyOnline)
+        } else {
+            Button("Unpublish") {
+                isShowingUnpublishConfirmation = true
+            }
+            .disabled(!isEffectivelyOnline)
         }
-        .disabled(!isEffectivelyOnline)
         Button("Archive…") {
             isShowingArchiveConfirmation = true
         }
@@ -697,6 +931,35 @@ struct DocumentReaderView: View {
 /// char-wraps code blocks, no way to opt out without forking the package)
 /// throws this off — every row below it reads one line low. Documented in
 /// TODO.local.md alongside the same package's other gaps.
+/// Thin vertical bar next to an anchored comment's text — same visual
+/// language as Word/Google Docs' margin comment indicators. Tapping opens
+/// the comments sheet focused to that thread.
+private struct CommentAnchorMarker: View {
+    let rect: CGRect
+    let onTap: () -> Void
+
+    private static let width: CGFloat = 3
+    private static let gap: CGFloat = 4
+    private static let hitTargetWidth: CGFloat = 16
+
+    var body: some View {
+        Color.clear
+            .frame(width: Self.hitTargetWidth, height: max(rect.height, 4))
+            .contentShape(Rectangle())
+            .overlay {
+                RoundedRectangle(cornerRadius: 1.5)
+                    .fill(Color.blue.opacity(0.6))
+                    .frame(width: Self.width)
+            }
+            .position(
+                x: rect.minX - Self.gap - Self.width / 2,
+                y: rect.minY + rect.height / 2
+            )
+            .onTapGesture(perform: onTap)
+            .help("View comment")
+    }
+}
+
 private struct CodeBlockLineNumberGutter: View {
     let selection: CodeBlockSelection
     let gutterWidth: CGFloat
@@ -731,4 +994,44 @@ 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/Features/Collections/DocumentReaderViewModel.swift

@@ -9,6 +9,9 @@ final class DocumentReaderViewModel {
     var emoji: String?
     var text: String
     var collectionId: String?
+    var parentDocumentId: String?
+    /// `nil` = draft (not published/visible to other workspace members).
+    var publishedAt: Date?
     var isFullWidth = false
     var isLoading = false
     var errorMessage: String?
@@ -76,6 +79,8 @@ final class DocumentReaderViewModel {
         self.emoji = document.emoji
         self.text = document.text
         self.collectionId = document.collectionId
+        self.parentDocumentId = document.parentDocumentId
+        self.publishedAt = document.publishedAt
         self.isFullWidth = document.fullWidth ?? false
         self.separateEditingEnabled = separateEditingEnabled
         self.lastSyncedText = document.text
@@ -95,6 +100,8 @@ final class DocumentReaderViewModel {
             emoji = full.emoji
             text = full.text
             collectionId = full.collectionId
+            parentDocumentId = full.parentDocumentId
+            publishedAt = full.publishedAt
             isFullWidth = full.fullWidth ?? false
             lastSyncedText = full.text
             lastSyncedTitle = full.title

Outpost/Features/Collections/NewDocumentSheet.swift

@@ -71,7 +71,7 @@ struct NewDocumentSheet: View {
                 ProgressView().frame(maxWidth: .infinity)
             } else {
                 Picker("Collection", selection: $selectedCollectionID) {
-                    Text("Choose a collection").tag(String?.none)
+                    Text("Draft (not published)").tag(String?.none)
                     ForEach(collections) { collection in
                         Text(collection.name).tag(Optional(collection.id))
                     }
@@ -86,6 +86,12 @@ struct NewDocumentSheet: View {
                 }
                 .labelsHidden()
                 .disabled(selectedCollectionID == nil || isLoadingDestinationDocuments)
+
+                if selectedCollectionID != nil {
+                    Label("This will publish the document immediately, making it visible to your workspace.", systemImage: "exclamationmark.triangle")
+                        .font(.caption)
+                        .foregroundStyle(.orange)
+                }
             }
 
             if let errorMessage {
@@ -97,18 +103,24 @@ struct NewDocumentSheet: View {
             HStack {
                 Spacer()
                 Button("Cancel", role: .cancel) { dismiss() }
-                Button("Create") {
+                Button(selectedCollectionID == nil ? "Save as Draft" : "Create & Publish") {
                     Task { await create() }
                 }
                 .keyboardShortcut(.defaultAction)
-                .disabled(selectedCollectionID == nil || isCreating)
+                .disabled(isCreating)
             }
         }
         .padding(20)
         .frame(width: 380)
         .task {
             await loadCollections()
-            selectedCollectionID = initialCollectionID ?? initialParentDocument?.collectionId ?? collections.first?.id
+            // "By default" means a bare New Document (Home, reader
+            // toolbar) starts as a draft — no `collections.first` fallback
+            // like there used to be. A contextual entry point (right-click
+            // a specific collection/document) still pre-fills that
+            // location, since that already carries clear placement intent;
+            // the publish warning above still applies to it either way.
+            selectedCollectionID = initialCollectionID ?? initialParentDocument?.collectionId
             selectedParentID = initialParentDocument?.id
             isTitleFocused = true
         }
@@ -147,7 +159,6 @@ struct NewDocumentSheet: View {
     }
 
     private func create() async {
-        guard let selectedCollectionID else { return }
         isCreating = true
         defer { isCreating = false }
         do {
@@ -156,7 +167,12 @@ struct NewDocumentSheet: View {
                     title: title.isEmpty ? "Untitled" : title,
                     text: "",
                     collectionId: selectedCollectionID,
-                    parentDocumentId: selectedParentID
+                    parentDocumentId: selectedParentID,
+                    // No collection/parent selected = draft; Outline can't
+                    // publish without one of the two regardless of this
+                    // flag, but setting it explicitly rather than relying
+                    // on that keeps intent obvious at the call site.
+                    publish: selectedCollectionID != nil
                 )
             )
             onCreated(document)

Outpost/Features/Collections/PublishDocumentSheet.swift

@@ -0,0 +1,144 @@
+#if os(macOS)
+import SwiftUI
+import OutlineKit
+
+/// Destination picker for publishing a draft — same collection-then-
+/// optional-parent-document shape as `MoveDocumentSheet`, since Outline's
+/// own web app treats "where does this go" identically for both actions.
+/// Pre-selects the document's own `collectionId`/`parentDocumentId` when it
+/// already has one (a draft can already belong to a collection without
+/// being published) rather than starting blank, per explicit instruction.
+///
+/// Publishing itself is two calls, not one: `documents.update(publish:
+/// true, collectionId:)` does the actual publish and top-level collection
+/// placement in one round-trip (confirmed from a live network capture);
+/// nesting under a specific parent document isn't a documented
+/// `documents.update` field, so that part reuses `documents.move` — the
+/// same already-working mechanism `MoveDocumentSheet` uses — as a second
+/// step, only when a parent was actually chosen.
+@MainActor
+struct PublishDocumentSheet: View {
+    @Environment(\.dismiss) private var dismiss
+
+    let apiClient: OutlineAPIClient
+    let document: OutlineDocument
+    let onPublished: () 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 isPublishing = false
+    @State private var errorMessage: String?
+
+    var body: some View {
+        VStack(alignment: .leading, spacing: 16) {
+            Text("Publish \"\(document.title.isEmpty ? "Untitled" : document.title)\"")
+                .font(.headline)
+            Text("Choose where this document should live once published.")
+                .font(.callout)
+                .foregroundStyle(.secondary)
+
+            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("Publish") {
+                    Task { await publish() }
+                }
+                .disabled(selectedCollectionID == nil || isPublishing)
+            }
+        }
+        .padding(20)
+        .frame(width: 360)
+        .task {
+            await loadCollections()
+            selectedCollectionID = document.collectionId
+            selectedParentID = document.parentDocumentId
+        }
+        .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 publish() async {
+        guard let selectedCollectionID else { return }
+        isPublishing = true
+        defer { isPublishing = false }
+        do {
+            _ = try await apiClient.updateDocument(
+                UpdateDocumentRequest(id: document.id, collectionId: selectedCollectionID, publish: true)
+            )
+            // Only a documents.move call actually supports parentDocumentId —
+            // skip it entirely when publishing straight to the collection root,
+            // the update above already placed it there.
+            if let selectedParentID {
+                try await apiClient.moveDocument(
+                    MoveDocumentRequest(id: document.id, collectionId: selectedCollectionID, parentDocumentId: selectedParentID)
+                )
+            }
+            await onPublished()
+            dismiss()
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Couldn't publish this document.")
+        }
+    }
+}
+#endif

Outpost/Features/Home/HomeTab.swift

@@ -5,6 +5,7 @@ enum HomeTab: String, CaseIterable, Identifiable {
     case popular = "Popular"
     case recentlyUpdated = "Recently Updated"
     case createdByMe = "Created by Me"
+    case drafts = "Drafts"
 
     var id: String { rawValue }
 }

Outpost/Features/Home/HomeViewModel.swift

@@ -10,6 +10,7 @@ final class HomeViewModel {
     private(set) var popular: [OutlineDocument] = []
     private(set) var recentlyUpdated: [OutlineDocument] = []
     private(set) var createdByMe: [OutlineDocument] = []
+    private(set) var drafts: [OutlineDocument] = []
 
     var isLoadingPinned = false
     var isLoadingTab = false
@@ -32,6 +33,7 @@ final class HomeViewModel {
         case .popular: popular
         case .recentlyUpdated: recentlyUpdated
         case .createdByMe: createdByMe
+        case .drafts: drafts
         }
     }
 
@@ -115,6 +117,8 @@ final class HomeViewModel {
             return try await apiClient.documentsList(
                 DocumentsListRequest(userId: userId, sort: "createdAt", direction: "DESC", limit: 25)
             )
+        case .drafts:
+            return try await apiClient.listDrafts(ListDraftsRequest(limit: 25))
         }
     }
 
@@ -124,6 +128,7 @@ final class HomeViewModel {
         case .popular: popular = documents
         case .recentlyUpdated: recentlyUpdated = documents
         case .createdByMe: createdByMe = documents
+        case .drafts: drafts = documents
         }
     }
 

Outpost/OutpostApp.swift

@@ -34,6 +34,7 @@ struct OutpostApp: App {
                 .onAppear { applyMacAppearance() }
                 .onChange(of: appearance) { _, _ in applyMacAppearance() }
                 .logoutConfirmationDialog(isPresented: $isShowingLogoutConfirmation, session: session)
+                .background(TransparentTitlebarWindowAccessor())
                 #endif
         }
         #if os(macOS)
@@ -101,3 +102,27 @@ struct OutpostApp: App {
     }
     #endif
 }
+
+#if os(macOS)
+/// Makes the titlebar/toolbar strip blend into the sidebar's own background
+/// instead of reading as a separate bar — same look as Mail/Notes/Finder.
+/// SwiftUI's `WindowGroup` exposes no direct hook for this, so this reaches
+/// into the underlying `NSWindow` the way `applyMacAppearance()` above
+/// reaches into `NSApp` for the same reason (no SwiftUI-level API exists).
+/// A `View` (not the window itself) is what actually needs to extend under
+/// the now-transparent titlebar — `.fullSizeContentView` just makes room;
+/// the sidebar's `.background` already does the rest with no other change.
+private struct TransparentTitlebarWindowAccessor: NSViewRepresentable {
+    func makeNSView(context: Context) -> NSView {
+        let view = NSView()
+        DispatchQueue.main.async {
+            guard let window = view.window else { return }
+            window.titlebarAppearsTransparent = true
+            window.styleMask.insert(.fullSizeContentView)
+        }
+        return view
+    }
+
+    func updateNSView(_ nsView: NSView, context: Context) {}
+}
+#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/ClosureMenuItem.swift

@@ -0,0 +1,25 @@
+#if os(macOS)
+import AppKit
+
+/// `NSMenuItem` has no closure-based initializer — the standard AppKit
+/// pattern is a small subclass that's its own target/action, so callers can
+/// just pass a Swift closure instead of wiring up a selector by hand.
+final class ClosureMenuItem: NSMenuItem {
+    private let handler: () -> Void
+
+    init(title: String, handler: @escaping () -> Void) {
+        self.handler = handler
+        super.init(title: title, action: #selector(invokeHandler), keyEquivalent: "")
+        self.target = self
+    }
+
+    @available(*, unavailable)
+    required init(coder: NSCoder) {
+        fatalError("init(coder:) has not been implemented")
+    }
+
+    @objc private func invokeHandler() {
+        handler()
+    }
+}
+#endif

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/Styling/MarkdownStyler+Images.swift

@@ -75,6 +75,7 @@ extension MarkdownStyler {
                     paragraphSpacing: imageEmbedConfig.paragraphSpacing,
                     alignment: .left,
                     mode: .visibleSource(imageGap: imageEmbedConfig.imageGap),
+                    restyleOnWidthChange: true,
                     ctx: ctx,
                     attrs: &attrs
                 )
@@ -88,6 +89,7 @@ extension MarkdownStyler {
                     paragraphSpacing: imageEmbedConfig.paragraphSpacing,
                     alignment: .left,
                     mode: .collapsedSource(markerTexts: ["![", "]", "(", ")"]),
+                    restyleOnWidthChange: true,
                     ctx: ctx,
                     attrs: &attrs
                 )
@@ -166,6 +168,7 @@ extension MarkdownStyler {
                         paragraphSpacing: imageEmbedConfig.paragraphSpacing,
                         alignment: .left,
                         mode: .visibleSource(imageGap: imageEmbedConfig.imageGap),
+                        restyleOnWidthChange: true,
                         ctx: ctx,
                         attrs: &attrs
                     )
@@ -179,6 +182,7 @@ extension MarkdownStyler {
                         paragraphSpacing: imageEmbedConfig.paragraphSpacing,
                         alignment: .left,
                         mode: .collapsedSource(markerTexts: ["![[", "]]"]),
+                        restyleOnWidthChange: true,
                         ctx: ctx,
                         attrs: &attrs
                     )

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

@@ -0,0 +1,44 @@
+//
+//  CommentAnchor.swift
+//  MarkdownEngine
+//
+//  Lets an embedder ask "where on screen is this text?" for arbitrary
+//  plain-text needles (e.g. an anchored comment's `anchorText`) that the
+//  engine has no concept of on its own — it doesn't know what a comment is,
+//  it just resolves a search term to a rect the same way it already
+//  resolves code-block token ranges.
+//
+
+import SwiftUI
+
+/// A plain-text search term the embedder wants a screen rect for, tagged
+/// with an opaque id so results can be matched back to whatever the
+/// embedder cares about (e.g. a comment id). Engine does a first-occurrence
+/// substring search against the current display text — no fuzzier
+/// disambiguation than that, since the engine has no positional data to
+/// work from beyond the text itself.
+public struct CommentAnchorQuery: Sendable, Equatable {
+    public let id: String
+    public let anchorText: String
+
+    public init(id: String, anchorText: String) {
+        self.id = id
+        self.anchorText = anchorText
+    }
+}
+
+/// Resolved screen rect for one ``CommentAnchorQuery``. Delivered through
+/// ``NativeTextViewWrapper/onCommentAnchorRectsChange`` — queries whose
+/// `anchorText` isn't found in the current text (deleted, edited past
+/// recognition) simply don't appear in the result.
+public struct CommentAnchorRect: Identifiable, Sendable {
+    public let id: String
+    /// Frame of the matched text in the text view's coordinate space —
+    /// same coordinate system as ``CodeBlockSelection/rect``.
+    public let rect: CGRect
+
+    public init(id: String, rect: CGRect) {
+        self.id = id
+        self.rect = rect
+    }
+}

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

@@ -0,0 +1,33 @@
+//
+//  NativeTextViewCoordinator+CommentAnchors.swift
+//  MarkdownEngine
+//
+//  Resolves embedder-supplied CommentAnchorQuery search terms to on-screen
+//  rects, the same viewRect(forCharacterRange:using:) utility the code-block
+//  copy-button overlay already uses. Deliberately no per-keystroke caching
+//  like updateCodeBlockSelection has — queries only change when the
+//  embedder's comment list changes (rare), not every keystroke, so the
+//  first-occurrence substring search + a handful of viewRect calls is cheap
+//  enough to just always redo.
+//
+
+import AppKit
+
+extension NativeTextViewCoordinator {
+    func updateCommentAnchorRects(textView: NSTextView) {
+        guard !commentAnchorQueries.isEmpty else {
+            onCommentAnchorRectsChange?([])
+            return
+        }
+        let nsText = textView.string as NSString
+        var results: [CommentAnchorRect] = []
+        for query in commentAnchorQueries {
+            guard !query.anchorText.isEmpty else { continue }
+            let found = nsText.range(of: query.anchorText)
+            guard found.location != NSNotFound,
+                  let rect = textView.viewRect(forCharacterRange: found, using: layoutBridge) else { continue }
+            results.append(CommentAnchorRect(id: query.id, rect: rect))
+        }
+        onCommentAnchorRectsChange?(results)
+    }
+}

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

@@ -337,6 +337,7 @@ extension NativeTextViewCoordinator {
 
         PerfTrace.measure("restyle") { restyleTextView(tv, paragraphCandidates: effectiveParagraphCandidates, tokens: tokens, classified: parsed.classified, blocks: parsed.blocks) }
         PerfTrace.measure("codeSel") { updateCodeBlockSelection(textView: tv, parsed: parsed) }
+        updateCommentAnchorRects(textView: tv)
         if wtActive {
             previousActiveTokenIndices = activeTokenIndices
             PerfTrace.end()
@@ -355,6 +356,14 @@ 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 }
@@ -692,6 +701,7 @@ extension NativeTextViewCoordinator {
         // Skip during a pending edit — viewRect is stale until textDidChange's restyle runs; otherwise the overlay flashes to the old Y before settling.
         if !shouldSkipSelectionRestyle {
             updateCodeBlockSelection(textView: tv, parsed: parsed)
+            updateCommentAnchorRects(textView: tv)
         }
     }
 

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

@@ -84,6 +84,9 @@ public final class NativeTextViewCoordinator: NSObject, NSTextViewDelegate {
     var onInlineSelectionChange: ((InlineSelectionState?) -> Void)?
     var onInlinePreviewKey: ((InlinePreviewKey) -> Bool)?
     var onCodeBlockSelectionChange: (([CodeBlockSelection]) -> Void)?
+    var onSelectedTextChange: ((String?) -> Void)?
+    var commentAnchorQueries: [CommentAnchorQuery] = []
+    var onCommentAnchorRectsChange: (([CommentAnchorRect]) -> 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 +109,7 @@ 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/NativeTextView/NativeTextView+FrameAndOverscroll.swift

@@ -269,21 +269,31 @@ extension NativeTextView {
 
         recalcOverscroll(for: scrollView, targetWidth: newSize.width, debugTag: "setFrameSize")
 
-        // Width change → only rendered table paragraphs need restyling. Their image
+        // Width change → only paragraphs tagged `.scrollableBlockFullRange`
-        // width can change, and an initially narrow table can become scrollable.
+        // (rendered tables and standalone images — see appendRenderedStandaloneBlock's
+        // `restyleOnWidthChange`) need restyling. Their display size is measured
+        // off the container width, and an initially narrow table can become
+        // scrollable.
         if widthChanged {
             DispatchQueue.main.async { [weak self] in
                 guard let self = self else { return }
                 if self.configuration.readingWidth == nil {
-                    self.restyleTableParagraphsForWidthChange()
+                    self.restyleWidthDependentParagraphsForWidthChange()
                 }
                 self.updateWideTableOverlays()
+                // Comment anchor bars are just as width-dependent as the
+                // table/image restyle above — wrapped lines reflow, shifting
+                // every anchor's y-position.
+                if let coordinator = self.delegate as? NativeTextViewCoordinator {
+                    coordinator.updateCommentAnchorRects(textView: self)
+                }
             }
         }
     }
 
-    /// Restyle only table paragraphs via stamped anchor ranges; avoids re-tokenizing the doc.
+    /// Restyle only width-dependent paragraphs (tables, standalone images) via
-    private func restyleTableParagraphsForWidthChange() {
+    /// stamped anchor ranges; avoids re-tokenizing the doc.
+    private func restyleWidthDependentParagraphsForWidthChange() {
         guard let storage = textStorage,
               let coord = delegate as? NativeTextViewCoordinator else { return }
         var ranges: [NSRange] = []

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 +99,19 @@ 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)?
+    /// Plain-text search terms the embedder wants a screen rect for — e.g.
+    /// anchored comments' `anchorText`, to draw an inline marker next to
+    /// them. See ``CommentAnchorQuery``/``CommentAnchorRect``.
+    public var commentAnchorQueries: [CommentAnchorQuery] = []
+    /// Fires whenever `commentAnchorQueries`' resolved positions change
+    /// (queries updated, or the document reflows). A query whose text isn't
+    /// found in the current document simply doesn't appear in the array.
+    public var onCommentAnchorRectsChange: (([CommentAnchorRect]) -> 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 +158,7 @@ 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 +171,9 @@ public struct NativeTextViewWrapper: NSViewRepresentable {
         onInlineSelectionChange: ((InlineSelectionState?) -> Void)? = nil,
         onInlinePreviewKey: ((InlinePreviewKey) -> Bool)? = nil,
         onCodeBlockSelectionChange: (([CodeBlockSelection]) -> Void)? = nil,
+        onSelectedTextChange: ((String?) -> Void)? = nil,
+        commentAnchorQueries: [CommentAnchorQuery] = [],
+        onCommentAnchorRectsChange: (([CommentAnchorRect]) -> Void)? = nil,
         onSpellCheckingPolicyChanged: ((SpellCheckingPolicy) -> Void)? = nil,
         placeholder: NSAttributedString? = nil,
         header: AnyView? = nil,
@@ -166,6 +187,7 @@ 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 +200,9 @@ public struct NativeTextViewWrapper: NSViewRepresentable {
         self.onInlineSelectionChange = onInlineSelectionChange
         self.onInlinePreviewKey = onInlinePreviewKey
         self.onCodeBlockSelectionChange = onCodeBlockSelectionChange
+        self.onSelectedTextChange = onSelectedTextChange
+        self.commentAnchorQueries = commentAnchorQueries
+        self.onCommentAnchorRectsChange = onCommentAnchorRectsChange
         self.onSpellCheckingPolicyChanged = onSpellCheckingPolicyChanged
         self.placeholder = placeholder
         self.header = header
@@ -328,6 +353,9 @@ public struct NativeTextViewWrapper: NSViewRepresentable {
         context.coordinator.onInlineSelectionChange = onInlineSelectionChange
         context.coordinator.onInlinePreviewKey = onInlinePreviewKey
         context.coordinator.onCodeBlockSelectionChange = onCodeBlockSelectionChange
+        context.coordinator.onSelectedTextChange = onSelectedTextChange
+        context.coordinator.onCommentAnchorRectsChange = onCommentAnchorRectsChange
+        context.coordinator.commentAnchorQueries = commentAnchorQueries
 
         textView.recalcOverscroll(for: scrollView)
         textView.setPlaceholder(placeholder)
@@ -541,6 +569,40 @@ 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)
+                }
+            }
+        }
+        // Comment queries can change (comments finished loading, resolved,
+        // etc.) with the document's own text completely unchanged — the
+        // "nothing to do" early-return just below would otherwise skip
+        // recomputing their positions forever. Handled the same way as
+        // imageChanged/wikiChanged just above: detect and act on it before
+        // that gate, independent of whether a real rebuild is happening.
+        if context.coordinator.commentAnchorQueries != commentAnchorQueries {
+            context.coordinator.commentAnchorQueries = commentAnchorQueries
+            let coordinator = context.coordinator
+            DispatchQueue.main.async { [weak textView] in
+                guard let textView else { return }
+                coordinator.updateCommentAnchorRects(textView: textView)
+            }
         }
         textView.isEditable = isEditable
         textView.isSelectable = true
@@ -562,6 +624,18 @@ 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 {
@@ -660,8 +734,10 @@ public struct NativeTextViewWrapper: NSViewRepresentable {
         }
         // Document rebuilds bypass textDidChange — re-derive emptiness here.
         textView.refreshPlaceholderVisibility()
+        context.coordinator.commentAnchorQueries = commentAnchorQueries
         DispatchQueue.main.async {
             context.coordinator.updateCodeBlockSelection(textView: textView)
+            context.coordinator.updateCommentAnchorRects(textView: textView)
         }
 
         context.coordinator.onCaretRectChange = onCaretRectChange
@@ -669,6 +745,8 @@ public struct NativeTextViewWrapper: NSViewRepresentable {
         context.coordinator.onInlineSelectionChange = onInlineSelectionChange
         context.coordinator.onInlinePreviewKey = onInlinePreviewKey
         context.coordinator.onCodeBlockSelectionChange = onCodeBlockSelectionChange
+        context.coordinator.onSelectedTextChange = onSelectedTextChange
+        context.coordinator.onCommentAnchorRectsChange = onCommentAnchorRectsChange
         context.coordinator.didInitialFormatting = true
     }
 
@@ -691,6 +769,9 @@ public struct NativeTextViewWrapper: NSViewRepresentable {
         coordinator.lastImageFingerprint = configuration.services.images.fingerprint()
         coordinator.lastWikiFingerprint = configuration.services.wikiLinks.fingerprint()
         coordinator.onCodeBlockSelectionChange = onCodeBlockSelectionChange
+        coordinator.onSelectedTextChange = onSelectedTextChange
+        coordinator.onCommentAnchorRectsChange = onCommentAnchorRectsChange
+        coordinator.commentAnchorQueries = commentAnchorQueries
         coordinator.onInlinePreviewKey = onInlinePreviewKey
         coordinator.userPrefersContinuousSpellChecking = configuration.spellChecking.continuousSpellChecking
         coordinator.userPrefersGrammarChecking = configuration.spellChecking.grammarChecking