diff --git a/SECURITY.md b/SECURITY.md
new file mode 100644
index 0000000..4b469d4
--- /dev/null
+++ b/SECURITY.md
@@ -0,0 +1,29 @@
+# Security Policy
+
+## Supported Versions
+
+Only the latest publicly released version of oAI is supported with security fixes. Please update to the latest version before reporting an issue, and confirm it still reproduces there.
+
+## Reporting a Vulnerability
+
+If you discover a security vulnerability in oAI, please report it privately rather than opening a public GitHub issue.
+
+To report a security concern, use the contact form at **[https://oai.pm/#contact](https://oai.pm/#contact)**.
+
+Please include as much detail as possible:
+- A description of the vulnerability and its potential impact
+- Steps to reproduce the issue
+- The oAI version and macOS version you're using
+- Any relevant logs (`~/Library/Logs/oAI.log`), with sensitive data redacted
+
+## Scope
+
+oAI is a native macOS app that stores conversations, settings, and API keys locally (SQLite database and Keychain). Areas of particular interest for security reports include:
+- API key handling and Keychain storage
+- MCP file access permission checks
+- Bash execution approval flow
+- Any path that could lead to data exfiltration or unauthorized local file/system access
+
+## Response
+
+Reports submitted through the contact form will be reviewed and acknowledged as soon as possible. Please allow time for a fix to be developed and released before any public disclosure.
diff --git a/oAI.xcodeproj/project.pbxproj b/oAI.xcodeproj/project.pbxproj
index 3e2321f..10b326d 100644
--- a/oAI.xcodeproj/project.pbxproj
+++ b/oAI.xcodeproj/project.pbxproj
@@ -15,9 +15,22 @@
 		A550A6622F3B72EA00136F2B /* oAI.app */ = {isa = PBXFileReference; explicitFileType = wrapper.application; includeInIndex = 0; path = oAI.app; sourceTree = BUILT_PRODUCTS_DIR; };
 /* End PBXFileReference section */
 
+/* Begin PBXFileSystemSynchronizedBuildFileExceptionSet section */
+		911C4D0E69E11B84C61453DC /* Exceptions for "oAI" folder in "oAI" target */ = {
+			isa = PBXFileSystemSynchronizedBuildFileExceptionSet;
+			membershipExceptions = (
+				Info.plist,
+			);
+			target = A550A6612F3B72EA00136F2B /* oAI */;
+		};
+/* End PBXFileSystemSynchronizedBuildFileExceptionSet section */
+
 /* Begin PBXFileSystemSynchronizedRootGroup section */
 		A550A6642F3B72EA00136F2B /* oAI */ = {
 			isa = PBXFileSystemSynchronizedRootGroup;
+			exceptions = (
+				911C4D0E69E11B84C61453DC /* Exceptions for "oAI" folder in "oAI" target */,
+			);
 			path = oAI;
 			sourceTree = "<group>";
 		};
@@ -270,6 +283,7 @@
 				ENABLE_PREVIEWS = YES;
 				ENABLE_USER_SELECTED_FILES = readonly;
 				GENERATE_INFOPLIST_FILE = YES;
+				INFOPLIST_FILE = "oAI/Info.plist";
 				INFOPLIST_KEY_LSApplicationCategoryType = "public.app-category.utilities";
 				INFOPLIST_KEY_NSCalendarsFullAccessUsageDescription = "oAI can read and create calendar events when you ask it to, if you enable Calendar access in Settings.";
 				INFOPLIST_KEY_NSContactsUsageDescription = "oAI can search your contacts when you ask it to, if you enable Contacts access in Settings.";
@@ -289,7 +303,7 @@
 				LD_RUNPATH_SEARCH_PATHS = "@executable_path/Frameworks";
 				"LD_RUNPATH_SEARCH_PATHS[sdk=macosx*]" = "@executable_path/../Frameworks";
 				MACOSX_DEPLOYMENT_TARGET = 26.2;
-				MARKETING_VERSION = 2.4.1;
+				MARKETING_VERSION = 2.4.2;
 				PRODUCT_BUNDLE_IDENTIFIER = com.oai.oAI;
 				PRODUCT_NAME = "$(TARGET_NAME)";
 				REGISTER_APP_GROUPS = YES;
@@ -319,6 +333,7 @@
 				ENABLE_PREVIEWS = YES;
 				ENABLE_USER_SELECTED_FILES = readonly;
 				GENERATE_INFOPLIST_FILE = YES;
+				INFOPLIST_FILE = "oAI/Info.plist";
 				INFOPLIST_KEY_LSApplicationCategoryType = "public.app-category.utilities";
 				INFOPLIST_KEY_NSCalendarsFullAccessUsageDescription = "oAI can read and create calendar events when you ask it to, if you enable Calendar access in Settings.";
 				INFOPLIST_KEY_NSContactsUsageDescription = "oAI can search your contacts when you ask it to, if you enable Contacts access in Settings.";
@@ -338,7 +353,7 @@
 				LD_RUNPATH_SEARCH_PATHS = "@executable_path/Frameworks";
 				"LD_RUNPATH_SEARCH_PATHS[sdk=macosx*]" = "@executable_path/../Frameworks";
 				MACOSX_DEPLOYMENT_TARGET = 26.2;
-				MARKETING_VERSION = 2.4.1;
+				MARKETING_VERSION = 2.4.2;
 				PRODUCT_BUNDLE_IDENTIFIER = com.oai.oAI;
 				PRODUCT_NAME = "$(TARGET_NAME)";
 				REGISTER_APP_GROUPS = YES;
diff --git a/oAI/Resources/oAI.help/Contents/Resources/en.lproj/index.html b/oAI/Resources/oAI.help/Contents/Resources/en.lproj/index.html
index 7592fe8..1f9bca2 100644
--- a/oAI/Resources/oAI.help/Contents/Resources/en.lproj/index.html
+++ b/oAI/Resources/oAI.help/Contents/Resources/en.lproj/index.html
@@ -20,7 +20,11 @@
 
         <nav class="toc">
             <h2>Contents</h2>
-            <ul>
+            <div class="toc-search">
+                <input type="search" id="tocSearch" placeholder="Search help topics…" aria-label="Search help topics">
+            </div>
+            <p id="tocNoResults" class="toc-no-results" hidden>No topics match your search.</p>
+            <ul id="tocList">
                 <li><a href="#getting-started">Getting Started</a></li>
                 <li><a href="#providers">AI Providers &amp; API Keys</a></li>
                 <li><a href="#models">Selecting Models</a></li>
@@ -1526,9 +1530,6 @@ Whenever the user asks you to translate something, translate it to Norwegian Bok
                     <dt><kbd>⌘,</kbd></dt>
                     <dd>Open Settings</dd>
 
-                    <dt><kbd>⌘/</kbd></dt>
-                    <dd>Show in-app Help</dd>
-
                     <dt><kbd>⌘?</kbd></dt>
                     <dd>Open this Help (macOS Help)</dd>
 
@@ -1815,5 +1816,37 @@ Whenever the user asks you to translate something, translate it to Norwegian Bok
             <p>© 2026 oAI - Rune Olsen. For support or feedback, visit <a href="https://gitlab.pm/rune/oai-swift">gitlab.pm</a> or <a href="mailto:support@fubar.pm?subject=oAI Support&body=What can I help you with?">Contact Us</a>.</p>
         </footer>
     </div>
+
+    <script>
+        (function () {
+            var searchInput = document.getElementById('tocSearch');
+            var tocList = document.getElementById('tocList');
+            var noResults = document.getElementById('tocNoResults');
+            if (!searchInput || !tocList) return;
+
+            var entries = Array.prototype.map.call(tocList.querySelectorAll('li'), function (li) {
+                var link = li.querySelector('a');
+                var id = link ? link.getAttribute('href').slice(1) : null;
+                var section = id ? document.getElementById(id) : null;
+                return {
+                    li: li,
+                    text: (section ? section.textContent : li.textContent).toLowerCase()
+                };
+            });
+
+            searchInput.addEventListener('input', function () {
+                var query = searchInput.value.trim().toLowerCase();
+                var visibleCount = 0;
+
+                entries.forEach(function (entry) {
+                    var matches = query === '' || entry.text.indexOf(query) !== -1;
+                    entry.li.hidden = !matches;
+                    if (matches) visibleCount++;
+                });
+
+                noResults.hidden = visibleCount > 0;
+            });
+        })();
+    </script>
 </body>
 </html>
diff --git a/oAI/Resources/oAI.help/Contents/Resources/en.lproj/styles.css b/oAI/Resources/oAI.help/Contents/Resources/en.lproj/styles.css
index f7e372a..7518e9c 100644
--- a/oAI/Resources/oAI.help/Contents/Resources/en.lproj/styles.css
+++ b/oAI/Resources/oAI.help/Contents/Resources/en.lproj/styles.css
@@ -101,6 +101,32 @@ nav.toc h2 {
     margin-bottom: 16px;
 }
 
+.toc-search {
+    margin-bottom: 16px;
+}
+
+.toc-search input[type="search"] {
+    width: 100%;
+    font-family: inherit;
+    font-size: 15px;
+    padding: 10px 14px;
+    color: var(--text-primary);
+    background: var(--background);
+    border: 1px solid var(--border);
+    border-radius: 8px;
+    outline: none;
+}
+
+.toc-search input[type="search"]:focus {
+    border-color: var(--primary-color);
+}
+
+.toc-no-results {
+    font-size: 14px;
+    color: var(--text-secondary);
+    margin-bottom: 0;
+}
+
 nav.toc ul {
     list-style: none;
 }
diff --git a/oAI/Services/BackupService.swift b/oAI/Services/BackupService.swift
index 36b52ff..e65b89a 100644
--- a/oAI/Services/BackupService.swift
+++ b/oAI/Services/BackupService.swift
@@ -34,6 +34,15 @@ struct BackupManifest: Codable {
     let credentials: [String: String]?
 }
 
+// MARK: - FavoritesPayload
+
+/// Small standalone file (separate from the full settings backup) so starring a model
+/// syncs near-instantly across machines instead of waiting for the next full backup.
+struct FavoritesPayload: Codable {
+    let updatedAt: String
+    let ids: [String]
+}
+
 // MARK: - BackupService
 
 @Observable
@@ -51,6 +60,8 @@ final class BackupService {
     /// URL of the last backup file
     var lastBackupURL: URL?
 
+    private var autoBackupTimer: Timer?
+
     // Keys excluded from backup — encrypted_ prefix + internal migration flags
     private static let excludedKeys: Set<String> = [
         "encrypted_openrouterAPIKey",
@@ -71,6 +82,7 @@ final class BackupService {
 
     private init() {
         checkForExistingBackup()
+        startAutoBackupTimer()
     }
 
     // MARK: - iCloud Path Resolution
@@ -176,6 +188,88 @@ final class BackupService {
         log.info("Restored \(manifest.settings.count) settings from backup (v\(manifest.version))")
     }
 
+    // MARK: - Favorite Models Sync
+
+    private func favoritesFileURL() -> URL {
+        resolveBackupDirectory().appendingPathComponent("oai_favorites.json")
+    }
+
+    /// Write the current local favorites to iCloud Drive. Called whenever a favorite is toggled.
+    func pushFavorites() async {
+        let settings = SettingsService.shared
+        let payload = FavoritesPayload(
+            updatedAt: settings.favoriteModelsUpdatedAt,
+            ids: settings.favoriteModelIds.sorted()
+        )
+        guard let data = try? JSONEncoder().encode(payload) else { return }
+        try? data.write(to: favoritesFileURL(), options: .atomic)
+        log.debug("Pushed \(payload.ids.count) favorite model(s) to iCloud")
+    }
+
+    /// Reconcile local favorites with the iCloud copy using last-write-wins (by timestamp).
+    /// Call on launch (and optionally on app-become-active) to pick up changes from other machines.
+    func syncFavoritesOnLaunch() async {
+        let settings = SettingsService.shared
+        let fileURL = favoritesFileURL()
+
+        guard let data = try? Data(contentsOf: fileURL),
+              let remote = try? JSONDecoder().decode(FavoritesPayload.self, from: data) else {
+            // No remote copy yet — push local state (may be empty, that's fine).
+            await pushFavorites()
+            return
+        }
+
+        let localUpdatedAt = settings.favoriteModelsUpdatedAt
+        let localIds = settings.favoriteModelIds
+        if remote.updatedAt > localUpdatedAt {
+            settings.favoriteModelIds = Set(remote.ids)
+            settings.favoriteModelsUpdatedAt = remote.updatedAt
+            log.info("Applied \(remote.ids.count) favorite model(s) from iCloud (remote was newer)")
+        } else if localUpdatedAt > remote.updatedAt {
+            await pushFavorites()
+        } else if Set(remote.ids) != localIds {
+            // Tied timestamps (both empty is the common case: two machines that already had
+            // favorites before this sync feature existed, neither ever bumped the timestamp).
+            // Union rather than silently dropping one side's favorites.
+            settings.favoriteModelIds = localIds.union(remote.ids)
+            settings.favoriteModelsUpdatedAt = ISO8601DateFormatter().string(from: Date())
+            await pushFavorites()
+            log.info("Merged favorites from iCloud (tied timestamps) — union of \(localIds.count) local + \(remote.ids.count) remote")
+        }
+        // Equal timestamps and identical sets: already in sync, nothing to do.
+    }
+
+    // MARK: - Automatic Backup
+
+    private static let dailyInterval: TimeInterval = 24 * 3600
+    private static let weeklyInterval: TimeInterval = 7 * 24 * 3600
+
+    /// Checked once at launch and hourly thereafter while the app is running.
+    private func startAutoBackupTimer() {
+        Task { await checkAndPerformAutoBackupIfDue() }
+        autoBackupTimer = Timer.scheduledTimer(withTimeInterval: 3600, repeats: true) { [weak self] _ in
+            Task { await self?.checkAndPerformAutoBackupIfDue() }
+        }
+    }
+
+    func checkAndPerformAutoBackupIfDue() async {
+        let frequency = SettingsService.shared.autoBackupFrequency
+        let interval: TimeInterval
+        switch frequency {
+        case "daily": interval = Self.dailyInterval
+        case "weekly": interval = Self.weeklyInterval
+        default: return // "manual" — user triggers backups by hand
+        }
+
+        checkForExistingBackup()
+        if let last = lastBackupDate, Date().timeIntervalSince(last) < interval {
+            return // not due yet
+        }
+
+        log.info("Automatic backup (\(frequency, privacy: .public)) is due — backing up now")
+        _ = try? await exportSettings()
+    }
+
     // MARK: - Helpers
 
     private func appVersion() -> String {
diff --git a/oAI/Services/ContactsService.swift b/oAI/Services/ContactsService.swift
index 058ab42..1863c4e 100644
--- a/oAI/Services/ContactsService.swift
+++ b/oAI/Services/ContactsService.swift
@@ -63,7 +63,8 @@ class ContactsService {
             store.requestAccess(for: .contacts) { granted, error in
                 let after = CNContactStore.authorizationStatus(for: .contacts)
                 if let error {
-                    Log.mcp.error("ContactsService.requestAccess: error=\(error.localizedDescription); granted=\(granted); status after = \(Self.describe(after)) (raw=\(after.rawValue))")
+                    let nsError = error as NSError
+                    Log.mcp.error("ContactsService.requestAccess: error=\(error.localizedDescription) domain=\(nsError.domain) code=\(nsError.code) userInfo=\(nsError.userInfo); granted=\(granted); status after = \(Self.describe(after)) (raw=\(after.rawValue))")
                 } else {
                     Log.mcp.info("ContactsService.requestAccess: granted=\(granted); status after = \(Self.describe(after)) (raw=\(after.rawValue))")
                 }
diff --git a/oAI/Services/SettingsService.swift b/oAI/Services/SettingsService.swift
index 8c3060b..3f8088e 100644
--- a/oAI/Services/SettingsService.swift
+++ b/oAI/Services/SettingsService.swift
@@ -25,16 +25,11 @@ import Foundation
 import os
 import Security
 
-/// Kill switch for the Personal Data tools (Calendar/Reminders/Contacts/Location & Maps).
-/// Flip `isHiddenPendingAppleFix` back to `false` once Apple fixes the macOS 27 beta TCC bug
-/// (filed with Apple). Each flag hides the relevant UI and forces the `*Enabled` getter to
-/// return `false` regardless of the persisted DB value — no code deleted, just inert.
+/// Kill switch for the entire Personal Data tools section (Calendar/Reminders/Contacts/
+/// Location & Maps). Hides the UI and forces every `*Enabled` getter to return `false`
+/// regardless of the persisted DB value — no code deleted, just inert.
 enum PersonalDataTools {
-    /// Hides the entire Personal Data section. Flip to `false` once all four services work.
     static let isHiddenPendingAppleFix = false
-    /// Hides only the Contacts row. Contacts TCC still broken under hardened runtime on
-    /// macOS 27 beta 2 while Calendar/Reminders/Location are fixed. Flip to `false` once fixed.
-    static let isContactsHiddenPendingAppleFix = true
 }
 
 @Observable
@@ -520,10 +515,33 @@ class SettingsService {
         }
     }
 
+    /// ISO8601 timestamp of the last local change to favoriteModelIds — used to
+    /// resolve last-write-wins conflicts when syncing favorites across machines.
+    var favoriteModelsUpdatedAt: String {
+        get { cache["favoriteModelsUpdatedAt"] ?? "" }
+        set {
+            cache["favoriteModelsUpdatedAt"] = newValue
+            DatabaseService.shared.setSetting(key: "favoriteModelsUpdatedAt", value: newValue)
+        }
+    }
+
     func toggleFavoriteModel(_ id: String) {
         var favs = favoriteModelIds
         if favs.contains(id) { favs.remove(id) } else { favs.insert(id) }
         favoriteModelIds = favs
+        favoriteModelsUpdatedAt = ISO8601DateFormatter().string(from: Date())
+        Task { await BackupService.shared.pushFavorites() }
+    }
+
+    // MARK: - Automatic Backup
+
+    /// "manual" (default), "daily", or "weekly"
+    var autoBackupFrequency: String {
+        get { cache["autoBackupFrequency"] ?? "manual" }
+        set {
+            cache["autoBackupFrequency"] = newValue
+            DatabaseService.shared.setSetting(key: "autoBackupFrequency", value: newValue)
+        }
     }
 
     // MARK: - Anytype MCP Settings
@@ -695,7 +713,7 @@ class SettingsService {
     }
 
     var contactsEnabled: Bool {
-        get { !PersonalDataTools.isHiddenPendingAppleFix && !PersonalDataTools.isContactsHiddenPendingAppleFix && cache["contactsEnabled"] == "true" }
+        get { !PersonalDataTools.isHiddenPendingAppleFix && cache["contactsEnabled"] == "true" }
         set {
             cache["contactsEnabled"] = String(newValue)
             DatabaseService.shared.setSetting(key: "contactsEnabled", value: String(newValue))
diff --git a/oAI/ViewModels/ChatViewModel.swift b/oAI/ViewModels/ChatViewModel.swift
index ecc2dc8..7b3f88e 100644
--- a/oAI/ViewModels/ChatViewModel.swift
+++ b/oAI/ViewModels/ChatViewModel.swift
@@ -90,6 +90,7 @@ You are a helpful AI assistant. Follow these core principles:
 - **Be Direct**: Provide concise, relevant answers. No unnecessary preambles.
 - **Show Your Work**: If you use capabilities (tools, web search, etc.), demonstrate what you did.
 - **Complete Tasks Properly**: If you start something, finish it correctly.
+- **Match the User's Language**: Always reply in the same language the user is writing in, even when the request itself involves another language (e.g. a translation or spelling request) — the target language applies to the content you produce, not to your own reply.
 
 ## FORMATTING
 
diff --git a/oAI/Views/Main/ContentView.swift b/oAI/Views/Main/ContentView.swift
index a823094..f2d740b 100644
--- a/oAI/Views/Main/ContentView.swift
+++ b/oAI/Views/Main/ContentView.swift
@@ -29,7 +29,8 @@ import Darwin   // uname, sysctlbyname
 struct ContentView: View {
     @Environment(ChatViewModel.self) var chatViewModel
     private var updateService = UpdateCheckService.shared
-    @State private var columnVisibility: NavigationSplitViewVisibility = .all
+    @State private var columnVisibility: NavigationSplitViewVisibility =
+        SettingsService.shared.sidebarVisible ? .all : .detailOnly
     @State private var showIntelWarning = false
 
     var body: some View {
@@ -46,6 +47,9 @@ struct ContentView: View {
             )
         }
         .frame(minWidth: 860, minHeight: 560)
+        .onChange(of: columnVisibility) { _, newValue in
+            SettingsService.shared.sidebarVisible = newValue != .detailOnly
+        }
         #if os(macOS)
         .onAppear {
             NSApplication.shared.windows.forEach { $0.tabbingMode = .disallowed }
diff --git a/oAI/Views/Screens/HelpView.swift b/oAI/Views/Screens/HelpView.swift
index d290046..9063dd9 100644
--- a/oAI/Views/Screens/HelpView.swift
+++ b/oAI/Views/Screens/HelpView.swift
@@ -213,7 +213,6 @@ private let keyboardShortcuts: [(key: String, description: String)] = [
     ("\u{2318}L", "Conversations"),
     ("\u{21E7}\u{2318}S", "Statistics"),
     ("\u{2318},", "Settings"),
-    ("\u{2318}/", "Help"),
 ]
 
 // MARK: - HelpView
diff --git a/oAI/Views/Screens/SettingsView.swift b/oAI/Views/Screens/SettingsView.swift
index 809667b..0f3c8e7 100644
--- a/oAI/Views/Screens/SettingsView.swift
+++ b/oAI/Views/Screens/SettingsView.swift
@@ -125,6 +125,7 @@ You are a helpful AI assistant. Follow these core principles:
 - **Be Direct**: Provide concise, relevant answers. No unnecessary preambles.
 - **Show Your Work**: If you use capabilities (tools, web search, etc.), demonstrate what you did.
 - **Complete Tasks Properly**: If you start something, finish it correctly.
+- **Match the User's Language**: Always reply in the same language the user is writing in, even when the request itself involves another language (e.g. a translation or spelling request) — the target language applies to the content you produce, not to your own reply.
 
 ## FORMATTING
 
@@ -828,10 +829,6 @@ It's better to admit "I need more information" or "I cannot do that" than to fak
         externalMCPSection
 
         // MARK: Personal Data
-        // isHiddenPendingAppleFix hides the entire section (macOS 27 beta TCC bug).
-        // isContactsHiddenPendingAppleFix hides just the Contacts row (still broken in beta 2
-        // under hardened runtime while Calendar/Reminders/Location are fixed). Flip each flag
-        // to false once Apple ships a fix.
         if !PersonalDataTools.isHiddenPendingAppleFix {
         Divider()
 
@@ -842,18 +839,8 @@ It's better to admit "I need more information" or "I cannot do that" than to fak
                     .foregroundStyle(.teal)
                 Text("Personal Data")
                     .font(.system(size: 18, weight: .semibold))
-                if PersonalDataTools.isContactsHiddenPendingAppleFix {
-                    Text("β")
-                        .font(.system(size: 11, weight: .bold))
-                        .foregroundStyle(.orange)
-                        .padding(.horizontal, 5)
-                        .padding(.vertical, 2)
-                        .background(Color.orange.opacity(0.15))
-                        .clipShape(RoundedRectangle(cornerRadius: 4))
-                        .help("Beta Feature. May change.")
-                }
             }
-            Text("Let the AI access your Calendar, Reminders, and Location & Maps to answer questions about your schedule and surroundings. Each service is opt-in and uses standard macOS permission prompts. This functionality is in beta and may change.")
+            Text("Let the AI access your Calendar, Reminders, Contacts, and Location & Maps to answer questions about your schedule and surroundings. Each service is opt-in and uses standard macOS permission prompts. This functionality is in beta and may change.")
                 .font(.system(size: 14))
                 .foregroundStyle(.secondary)
                 .fixedSize(horizontal: false, vertical: true)
@@ -888,16 +875,14 @@ It's better to admit "I need more information" or "I cannot do that" than to fak
                     requestAccess: { remindersAccessState = await EventKitService.shared.requestReminderAccess() ? .granted : EventKitService.shared.reminderAccessState }
                 )
                 rowDivider()
-                if !PersonalDataTools.isContactsHiddenPendingAppleFix {
-                    personalDataRow(
-                        title: "Contacts",
-                        isEnabled: $settingsService.contactsEnabled,
-                        state: contactsAccessState,
-                        systemSettingsAnchor: "Privacy_Contacts",
-                        requestAccess: { contactsAccessState = await ContactsService.shared.requestAccess() ? .granted : ContactsService.shared.accessState }
-                    )
-                    rowDivider()
-                }
+                personalDataRow(
+                    title: "Contacts",
+                    isEnabled: $settingsService.contactsEnabled,
+                    state: contactsAccessState,
+                    systemSettingsAnchor: "Privacy_Contacts",
+                    requestAccess: { contactsAccessState = await ContactsService.shared.requestAccess() ? .granted : ContactsService.shared.accessState }
+                )
+                rowDivider()
                 personalDataRow(
                     title: "Location & Maps",
                     isEnabled: $settingsService.locationMapsEnabled,
@@ -2595,6 +2580,37 @@ It's better to admit "I need more information" or "I cannot do that" than to fak
                 }
             }
 
+            // Automatic Backup
+            VStack(alignment: .leading, spacing: 6) {
+                sectionHeader("Automatic Backup")
+                formSection {
+                    row("Frequency") {
+                        Picker("", selection: $settingsService.autoBackupFrequency) {
+                            Text("Off").tag("manual")
+                            Text("Daily").tag("daily")
+                            Text("Weekly").tag("weekly")
+                        }
+                        .pickerStyle(.segmented)
+                        .frame(width: 220)
+                    }
+                }
+                Text("When enabled, oAI backs up automatically in the background (checked at launch and hourly while running) — no need to press \"Back Up Now\" yourself.")
+                    .font(.system(size: 13))
+                    .foregroundStyle(.secondary)
+                    .fixedSize(horizontal: false, vertical: true)
+                    .padding(.horizontal, 4)
+            }
+
+            // Favorites Sync
+            VStack(alignment: .leading, spacing: 6) {
+                sectionHeader("Favorite Models")
+                Text("Starred models sync automatically via the same iCloud Drive folder — star a model on one Mac and it appears starred on your others within a launch or two.")
+                    .font(.system(size: 13))
+                    .foregroundStyle(.secondary)
+                    .fixedSize(horizontal: false, vertical: true)
+                    .padding(.horizontal, 4)
+            }
+
             // Actions
             VStack(alignment: .leading, spacing: 6) {
                 sectionHeader("Actions")
diff --git a/oAI/oAI.entitlements b/oAI/oAI.entitlements
index 97a7c31..a86f180 100644
--- a/oAI/oAI.entitlements
+++ b/oAI/oAI.entitlements
@@ -12,7 +12,7 @@
 	<true/>
 	<key>com.apple.security.personal-information.reminders</key>
 	<true/>
-	<key>com.apple.security.personal-information.contacts</key>
+	<key>com.apple.security.personal-information.addressbook</key>
 	<true/>
 	<key>com.apple.security.personal-information.location</key>
 	<true/>
diff --git a/oAI/oAIApp.swift b/oAI/oAIApp.swift
index de68282..132864d 100644
--- a/oAI/oAIApp.swift
+++ b/oAI/oAIApp.swift
@@ -43,6 +43,11 @@ struct oAIApp: App {
             await GitSyncService.shared.syncOnStartup()
         }
 
+        // Reconcile starred models with the iCloud copy (cross-machine favorites sync)
+        Task {
+            await BackupService.shared.syncFavoritesOnLaunch()
+        }
+
         // Check for updates in the background
         UpdateCheckService.shared.checkForUpdates()
     }
@@ -56,6 +61,11 @@ struct oAIApp: App {
                     AboutView()
                 }
                 #if os(macOS)
+                .onReceive(NotificationCenter.default.publisher(for: NSApplication.didBecomeActiveNotification)) { _ in
+                    Task {
+                        await BackupService.shared.syncFavoritesOnLaunch()
+                    }
+                }
                 .onReceive(NotificationCenter.default.publisher(for: NSApplication.willTerminateNotification)) { _ in
                     Task { @MainActor in ExternalMCPManager.shared.stopAll() }
                     Task {
@@ -116,8 +126,11 @@ struct oAIApp: App {
                 .disabled(chatViewModel.messages.filter { $0.role != .system }.isEmpty)
             }
 
-            // ── View menu ─────────────────────────────────────────────────
-            CommandMenu("View") {
+            // ── Chat menu ─────────────────────────────────────────────────
+            // Named "Chat" (not "View") to avoid colliding with the "View" menu
+            // macOS auto-adds for NavigationSplitView (Enter Full Screen, etc.) —
+            // two menus both titled "View" would otherwise appear in the menu bar.
+            CommandMenu("Chat") {
                 Button("Select Model") { chatViewModel.showModelSelector = true }
                     .keyboardShortcut("m", modifiers: .command)
 
@@ -132,9 +145,6 @@ struct oAIApp: App {
                 Button("Command History") { chatViewModel.showHistory = true }
                     .keyboardShortcut("h", modifiers: [.command, .shift])
 
-                Button("In-App Help") { chatViewModel.showHelp = true }
-                    .keyboardShortcut("/", modifiers: .command)
-
                 Button("Credits") { chatViewModel.showCredits = true }
 
                 Divider()
@@ -161,11 +171,12 @@ struct oAIApp: App {
 
     #if os(macOS)
     private func openHelp() {
+        // Opens the Help Book's index.html directly in the default browser rather than
+        // through NSHelpManager/Help Viewer — see CLAUDE.md's macOS 27 beta note for why
+        // (Apple's Tips.app replacement for Help Viewer can't resolve anchors on this beta).
+        // Revisit once macOS 27 reaches RC.
         if let helpBookURL = Bundle.main.url(forResource: "oAI.help", withExtension: nil) {
             NSWorkspace.shared.open(helpBookURL.appendingPathComponent("Contents/Resources/en.lproj/index.html"))
-        } else {
-            // Fallback to Apple Help if help book not found
-            NSHelpManager.shared.openHelpAnchor("", inBook: Bundle.main.object(forInfoDictionaryKey: "CFBundleHelpBookName") as? String)
         }
     }
     #endif