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/Requests/CreateCommentRequest.swift

@@ -3,19 +3,24 @@ 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). Anchored (text-selection) comments aren't
+/// id, never another reply's). `anchorText` creates an inline (anchored)
-/// supported here — that needs `anchorText`, out of scope for this app.
+/// comment instead of a document-level one — the first occurrence of that
-/// `text` is the documented markdown convenience field for `data`
+/// exact substring in the document's plain text is used, same as Outline's
-/// (a ProseMirror document) — simplest path for plain-text comment bodies,
+/// own web editor; `anchorPrefix`/`anchorSuffix` aren't sent (this app has
-/// no need to construct ProseMirror JSON by hand.
+/// 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) {
+    public init(documentId: String, parentCommentId: String? = nil, text: String, anchorText: String? = nil) {
         self.documentId = documentId
         self.parentCommentId = parentCommentId
         self.text = text
+        self.anchorText = anchorText
     }
 }

Outpost/Features/Collections/DocumentCommentsSheet.swift

@@ -6,10 +6,7 @@ import OutlineKit
 /// 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. Creating a NEW anchored comment (from a text selection) isn't
+/// document.
-/// supported here — only viewing/replying to ones already anchored via the
-/// web app, whose position `DocumentReaderView` resolves to an inline
-/// marker.
 @MainActor
 struct DocumentCommentsSheet: View {
     @Environment(\.dismiss) private var dismiss
@@ -20,6 +17,17 @@ struct DocumentCommentsSheet: View {
     /// 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.
@@ -33,6 +41,10 @@ struct DocumentCommentsSheet: View {
 
     @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 = ""
@@ -112,6 +124,7 @@ struct DocumentCommentsSheet: View {
         .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: {
@@ -253,8 +266,36 @@ struct DocumentCommentsSheet: View {
     // 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("Add a comment…", text: $newCommentText, axis: .vertical)
+                TextField(
+                    composingAnchorText == nil ? "Add a comment…" : "Comment on this text…",
+                    text: $newCommentText,
+                    axis: .vertical
+                )
                 .textFieldStyle(.roundedBorder)
                 .lineLimit(1...4)
                 .onSubmit { Task { await postNewComment() } }
@@ -267,6 +308,7 @@ struct DocumentCommentsSheet: View {
                     .disabled(newCommentText.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty)
                 }
             }
+        }
         .padding()
     }
 
@@ -312,10 +354,12 @@ struct DocumentCommentsSheet: View {
         defer { isPostingNewComment = false }
         do {
             let created = try await apiClient.createComment(
-                CreateCommentRequest(documentId: document.id, text: text)
+                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.")
         }
@@ -333,6 +377,7 @@ struct DocumentCommentsSheet: View {
             comments.append(created)
             replyText = ""
             replyingToThreadId = nil
+            onCommentsChanged?()
         } catch {
             actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't post this reply.")
         }

Outpost/Features/Collections/DocumentReaderView.swift

@@ -101,6 +101,9 @@ struct DocumentReaderView: View {
     /// 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
@@ -227,6 +230,7 @@ struct DocumentReaderView: View {
                 if let commentCount, commentCount > 0 {
                     Button {
                         focusedCommentId = nil
+                        pendingCommentAnchorText = nil
                         isShowingCommentsSheet = true
                     } label: {
                         Image(systemName: "bubble.left.and.bubble.right")
@@ -242,9 +246,6 @@ struct DocumentReaderView: View {
                             .background(.blue, in: Circle())
                             .offset(x: 0, y: -1)
                     }
-                    .sheet(isPresented: $isShowingCommentsSheet) {
-                        DocumentCommentsSheet(apiClient: apiClient, document: document, focusedCommentId: focusedCommentId)
-                    }
                 }
 
                 if isImagePlaygroundEnabled && isImagePlaygroundSupported {
@@ -374,6 +375,21 @@ 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
@@ -420,6 +436,24 @@ struct DocumentReaderView: View {
         ))
     }
 
+    /// 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
@@ -523,6 +557,7 @@ struct DocumentReaderView: View {
                             ),
                             documentId: viewModel.documentId,
                             isEditable: viewModel.isEffectivelyEditable,
+                            onBuildContextMenu: { menu, _ in addCommentMenuItem(to: menu) },
                             onCodeBlockSelectionChange: { readerCodeBlocks = $0 },
                             onSelectedTextChange: { currentSelectedText = $0 },
                             commentAnchorQueries: commentAnchorQueries,
@@ -536,6 +571,7 @@ struct DocumentReaderView: View {
                         ForEach(commentAnchorRects) { anchor in
                             CommentAnchorMarker(rect: anchor.rect) {
                                 focusedCommentId = anchor.id
+                                pendingCommentAnchorText = nil
                                 isShowingCommentsSheet = true
                             }
                         }
@@ -605,6 +641,7 @@ struct DocumentReaderView: View {
                         ),
                         documentId: viewModel.documentId,
                         isEditable: false,
+                        onBuildContextMenu: { menu, _ in addCommentMenuItem(to: menu) },
                         onCodeBlockSelectionChange: { previewCodeBlocks = $0 },
                         onSelectedTextChange: { currentSelectedText = $0 },
                         commentAnchorQueries: commentAnchorQueries,
@@ -618,6 +655,7 @@ struct DocumentReaderView: View {
                     ForEach(commentAnchorRects) { anchor in
                         CommentAnchorMarker(rect: anchor.rect) {
                             focusedCommentId = anchor.id
+                            pendingCommentAnchorText = nil
                             isShowingCommentsSheet = true
                         }
                     }

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