fix(collections): wire up sidebar Pin, drop dead Embeds field, real toggles

Smoke-tested against a live server: Pin didn't work from the sidebar
context menu, Subscribe/Unsubscribe worked, Enable Embeds didn't.

- Sidebar document context menu still had the pre-pins.*-support
  disabled Pin/Unsubscribe stubs from before that endpoint existed -
  only the reader's menu got updated at the time. Wired up real Pin
  (collection-scoped pins.list loaded once per CollectionDocumentsOutline,
  not per row - avoids an N+1 call storm); left Unsubscribe disabled
  there since subscriptions.list is per-document, with an accurate
  comment pointing at the reader's menu instead.
- documentEmbeds confirmed not a real field - removed from
  UpdateDocumentRequest entirely rather than leave a menu item that
  silently no-ops.
- Subscribe, Viewer Insights, and Full Width are now real Toggle menu
  items (checkmark reflects actual state) instead of static
  action buttons. Viewer Insights state is inferred from whether
  documents.insights succeeds/fails, since insightsEnabled isn't
  readable back off Document - heuristic, flagged in code.

OutlineKit/Sources/OutlineKit/Requests/UpdateDocumentRequest.swift

@@ -7,12 +7,6 @@ public struct UpdateDocumentRequest: Encodable, Sendable {
     public let append: Bool?
     public let fullWidth: Bool?
     public let insightsEnabled: Bool?
-    /// Not in the vendored spec's `Document`/`documents.update` shape at all
-    /// (only a workspace-level `documentEmbeds` flag exists there) — included
-    /// speculatively since the field may exist on newer self-hosted servers.
-    /// Unrecognized fields are typically ignored server-side rather than
-    /// rejected, so this is low-risk even if unsupported.
-    public let documentEmbeds: Bool?
 
     public init(
         id: String,
@@ -20,8 +14,7 @@ public struct UpdateDocumentRequest: Encodable, Sendable {
         text: String? = nil,
         append: Bool? = nil,
         fullWidth: Bool? = nil,
-        insightsEnabled: Bool? = nil,
+        insightsEnabled: Bool? = nil
-        documentEmbeds: Bool? = nil
     ) {
         self.id = id
         self.title = title
@@ -29,6 +22,5 @@ public struct UpdateDocumentRequest: Encodable, Sendable {
         self.append = append
         self.fullWidth = fullWidth
         self.insightsEnabled = insightsEnabled
-        self.documentEmbeds = documentEmbeds
     }
 }

Outpost/Features/Collections/CollectionDocumentsOutline.swift

@@ -9,6 +9,7 @@ import OutlineKit
 /// client-side rather than `collections.documents`.
 struct CollectionDocumentsOutline: View {
     let apiClient: OutlineAPIClient
+    let collection: OutlineCollection
     @State private var viewModel: DocumentsViewModel
     let sortOption: SidebarSortOption
     let refreshToken: Int
@@ -17,6 +18,11 @@ struct CollectionDocumentsOutline: View {
     /// toolbar render the real hierarchy instead of just the leaf title.
     let onSelectDocument: ([OutlineDocument]) -> Void
 
+    /// Loaded once per collection (`pins.list` is collection-scoped) rather
+    /// than per-row — a per-row `pins.list`/lookup would be an N+1 call for
+    /// every document in the tree.
+    @State private var pinsByDocumentID: [String: OutlinePin] = [:]
+
     private var tree: [DocumentNode] {
         buildDocumentTree(from: viewModel.documents, sortedBy: sortOption)
     }
@@ -30,6 +36,7 @@ struct CollectionDocumentsOutline: View {
         onSelectDocument: @escaping ([OutlineDocument]) -> Void
     ) {
         self.apiClient = apiClient
+        self.collection = collection
         _viewModel = State(initialValue: DocumentsViewModel(apiClient: apiClient, collection: collection))
         self.sortOption = sortOption
         self.refreshToken = refreshToken
@@ -56,13 +63,23 @@ struct CollectionDocumentsOutline: View {
                         depth: 0,
                         ancestors: [],
                         selectedDocumentID: selectedDocumentID,
+                        pinsByDocumentID: pinsByDocumentID,
                         onSelectDocument: onSelectDocument,
-                        onDocumentsChanged: { await viewModel.load() }
+                        onDocumentsChanged: { await viewModel.load() },
+                        onPinsChanged: { await loadPins() }
                     )
                 }
             }
         }
-        .task(id: refreshToken) { await viewModel.load() }
+        .task(id: refreshToken) {
+            await viewModel.load()
+            await loadPins()
+        }
+    }
+
+    private func loadPins() async {
+        guard let pins = try? await apiClient.listPins(ListPinsRequest(collectionId: collection.id)) else { return }
+        pinsByDocumentID = Dictionary(uniqueKeysWithValues: pins.map { ($0.documentId, $0) })
     }
 }
 
@@ -81,8 +98,10 @@ private struct DocumentNodeRow: View {
     /// Chain from root down to (not including) this node.
     let ancestors: [OutlineDocument]
     let selectedDocumentID: String?
+    let pinsByDocumentID: [String: OutlinePin]
     let onSelectDocument: ([OutlineDocument]) -> Void
     let onDocumentsChanged: () async -> Void
+    let onPinsChanged: () async -> Void
 
     @State private var isExpanded = false
 
@@ -172,8 +191,10 @@ private struct DocumentNodeRow: View {
                         depth: depth + 1,
                         ancestors: ancestors + [node.document],
                         selectedDocumentID: selectedDocumentID,
+                        pinsByDocumentID: pinsByDocumentID,
                         onSelectDocument: onSelectDocument,
-                        onDocumentsChanged: onDocumentsChanged
+                        onDocumentsChanged: onDocumentsChanged,
+                        onPinsChanged: onPinsChanged
                     )
                 }
             }
@@ -259,7 +280,11 @@ private struct DocumentNodeRow: View {
         Button(starStore.isStarred(documentId: node.document.id) ? "Unstar" : "Star") {
             Task { await star() }
         }
-        // No `subscriptions.*` endpoint in the API — nothing to back this with.
+        // subscriptions.* does exist and works (confirmed against a live
+        // server via the reader's menu) — not shown here because
+        // subscriptions.list is per-document, so reflecting accurate
+        // per-row state for every document in the tree would mean an N+1
+        // call storm. Use the reader's ⋯ menu instead.
         Button("Unsubscribe") {}
             .disabled(true)
 
@@ -305,9 +330,9 @@ private struct DocumentNodeRow: View {
         Button("New Document") {
             Task { await createChildDocument() }
         }
-        // No `pins.*` endpoint in the API — nothing to back this with.
+        Button(pinsByDocumentID[node.document.id] != nil ? "Unpin" : "Pin") {
-        Button("Pin") {}
+            Task { await togglePin() }
-            .disabled(true)
+        }
 
         Divider()
 
@@ -351,6 +376,19 @@ private struct DocumentNodeRow: View {
         }
     }
 
+    private func togglePin() async {
+        do {
+            if let pin = pinsByDocumentID[node.document.id] {
+                try await apiClient.deletePin(id: pin.id)
+            } else {
+                _ = try await apiClient.createPin(CreatePinRequest(documentId: node.document.id, collectionId: node.document.collectionId))
+            }
+            await onPinsChanged()
+        } catch {
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't update pin state.")
+        }
+    }
+
     private func rename() async {
         do {
             _ = try await apiClient.updateDocument(UpdateDocumentRequest(id: node.document.id, title: renameText))

Outpost/Features/Collections/DocumentReaderView.swift

@@ -133,6 +133,9 @@ struct DocumentReaderView: View {
         .task {
             await viewModel.loadPinAndSubscriptionState()
         }
+        .task {
+            await viewModel.loadInsightsEnabledState()
+        }
         .task {
             while !Task.isCancelled {
                 await viewModel.loadViewers()
@@ -249,9 +252,10 @@ struct DocumentReaderView: View {
         Button(starStore.isStarred(documentId: viewModel.documentId) ? "Unstar" : "Star") {
             Task { await star() }
         }
-        Button(viewModel.isSubscribed ? "Unsubscribe" : "Subscribe") {
+        Toggle("Subscribed", isOn: Binding(
-            Task { await toggleSubscription() }
+            get: { viewModel.isSubscribed },
-        }
+            set: { _ in Task { await toggleSubscription() } }
+        ))
 
         Divider()
 
@@ -323,15 +327,20 @@ struct DocumentReaderView: View {
 
         Divider()
 
-        Button("Enable Viewer Insights") {
+        Toggle("Viewer Insights", isOn: Binding(
-            Task { await enableInsights() }
+            get: { viewModel.isInsightsEnabled ?? false },
-        }
+            set: { _ in Task { await toggleInsights() } }
-        Button("Enable Embeds") {
+        ))
-            Task { await enableEmbeds() }
+        // Confirmed against a live server: there's no per-document embeds
-        }
+        // field. Only a workspace-level setting exists, and that's not
-        Button(viewModel.isFullWidth ? "Default Width" : "Full Width") {
+        // reachable via the API either (no `team.update` endpoint in the
-            Task { await toggleFullWidth() }
+        // vendored spec) — disabled rather than kept as a broken action.
-        }
+        Button("Enable Embeds") {}
+            .disabled(true)
+        Toggle("Full Width", isOn: Binding(
+            get: { viewModel.isFullWidth },
+            set: { _ in Task { await toggleFullWidth() } }
+        ))
 
         Divider()
 
@@ -372,19 +381,11 @@ struct DocumentReaderView: View {
         }
     }
 
-    private func enableInsights() async {
+    private func toggleInsights() async {
         do {
-            try await viewModel.enableViewerInsights()
+            try await viewModel.toggleViewerInsights()
         } catch {
-            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't enable viewer insights.")
+            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't update viewer insights.")
-        }
-    }
-
-    private func enableEmbeds() async {
-        do {
-            try await viewModel.enableEmbeds()
-        } catch {
-            actionErrorMessage = outlineErrorMessage(error, fallback: "Couldn't enable embeds.")
         }
     }
 

Outpost/Features/Collections/DocumentReaderViewModel.swift

@@ -30,6 +30,12 @@ final class DocumentReaderViewModel {
     private var subscriptionId: String?
     private(set) var share: OutlineShare?
 
+    /// `nil` until checked. Inferred from whether `documents.insights`
+    /// succeeds or fails — `insightsEnabled` isn't readable back off
+    /// `Document` in the vendored spec, so there's no direct field to read.
+    /// This is a heuristic, not confirmed server behavior.
+    private(set) var isInsightsEnabled: Bool?
+
     let documentId: String
     private let apiClient: OutlineAPIClient
 
@@ -98,6 +104,15 @@ final class DocumentReaderViewModel {
         share = try? await apiClient.shareInfo(documentId: documentId)
     }
 
+    func loadInsightsEnabledState() async {
+        do {
+            _ = try await apiClient.documentInsights(DocumentInsightsRequest(id: documentId))
+            isInsightsEnabled = true
+        } catch {
+            isInsightsEnabled = false
+        }
+    }
+
     func togglePin() async throws {
         if let pinId {
             self.pinId = nil
@@ -168,14 +183,14 @@ final class DocumentReaderViewModel {
         }
     }
 
-    /// Fire-and-forget: `insightsEnabled` isn't readable back off `Document`
+    func toggleViewerInsights() async throws {
-    /// in the vendored spec, so there's no state to reflect as a checkmark.
+        let newValue = !(isInsightsEnabled ?? false)
-    func enableViewerInsights() async throws {
+        isInsightsEnabled = newValue
-        _ = try await apiClient.updateDocument(UpdateDocumentRequest(id: documentId, insightsEnabled: true))
+        do {
+            _ = try await apiClient.updateDocument(UpdateDocumentRequest(id: documentId, insightsEnabled: newValue))
+        } catch {
+            isInsightsEnabled = !newValue
+            throw error
         }
-
-    /// Fire-and-forget, speculative field — see `UpdateDocumentRequest.documentEmbeds`.
-    func enableEmbeds() async throws {
-        _ = try await apiClient.updateDocument(UpdateDocumentRequest(id: documentId, documentEmbeds: true))
     }
 }