oAI.xcodeproj/project.pbxproj

@@ -279,7 +279,7 @@
 				LD_RUNPATH_SEARCH_PATHS = "@executable_path/Frameworks";
 				"LD_RUNPATH_SEARCH_PATHS[sdk=macosx*]" = "@executable_path/../Frameworks";
 				MACOSX_DEPLOYMENT_TARGET = 26.2;
-				MARKETING_VERSION = 2.3.3;
+				MARKETING_VERSION = 2.3.4;
 				PRODUCT_BUNDLE_IDENTIFIER = com.oai.oAI;
 				PRODUCT_NAME = "$(TARGET_NAME)";
 				REGISTER_APP_GROUPS = YES;
@@ -323,7 +323,7 @@
 				LD_RUNPATH_SEARCH_PATHS = "@executable_path/Frameworks";
 				"LD_RUNPATH_SEARCH_PATHS[sdk=macosx*]" = "@executable_path/../Frameworks";
 				MACOSX_DEPLOYMENT_TARGET = 26.2;
-				MARKETING_VERSION = 2.3.3;
+				MARKETING_VERSION = 2.3.4;
 				PRODUCT_BUNDLE_IDENTIFIER = com.oai.oAI;
 				PRODUCT_NAME = "$(TARGET_NAME)";
 				REGISTER_APP_GROUPS = YES;

oAI/Models/Message.swift

@@ -31,6 +31,14 @@ enum MessageRole: String, Codable {
     case system
 }
 
+/// Detail for a single tool call within a system "🔧 Calling:" message.
+/// Not persisted — in-memory only.
+struct ToolCallDetail {
+    let name: String
+    let input: String       // raw JSON string of arguments
+    var result: String?     // raw JSON string of result (nil while pending)
+}
+
 struct Message: Identifiable, Codable, Equatable {
     let id: UUID
     let role: MessageRole
@@ -52,6 +60,9 @@ struct Message: Identifiable, Codable, Equatable {
     // Generated images from image-output models (base64-decoded PNG/JPEG data)
     var generatedImages: [Data]? = nil
 
+    // Tool call details (not persisted — in-memory only for expandable display)
+    var toolCalls: [ToolCallDetail]? = nil
+
     init(
         id: UUID = UUID(),
         role: MessageRole,

oAI/Providers/AnthropicProvider.swift

@@ -318,7 +318,41 @@ class AnthropicProvider: AIProvider {
                     conversationMessages.append(["role": "assistant", "content": msg["content"] as? String ?? ""])
                 }
             } else {
-                conversationMessages.append(["role": role, "content": msg["content"] as? String ?? ""])
+                // Content may be a String (plain text) or an Array (image/multipart blocks)
+                if let contentArray = msg["content"] as? [[String: Any]] {
+                    // Convert image_url blocks (OpenAI format) to Anthropic image blocks
+                    let anthropicBlocks: [[String: Any]] = contentArray.compactMap { block in
+                        let type = block["type"] as? String ?? ""
+                        if type == "text" {
+                            return block
+                        } else if type == "image_url",
+                                  let imageUrl = block["image_url"] as? [String: Any],
+                                  let url = imageUrl["url"] as? String,
+                                  url.hasPrefix("data:") {
+                            // data:<mediaType>;base64,<data>
+                            let withoutData = url.dropFirst(5) // strip "data:"
+                            guard let semicolon = withoutData.firstIndex(of: ";"),
+                                  let comma = withoutData.firstIndex(of: ",") else { return nil }
+                            let mediaType = String(withoutData[withoutData.startIndex..<semicolon])
+                            let base64Data = String(withoutData[withoutData.index(after: comma)...])
+                            return [
+                                "type": "image",
+                                "source": [
+                                    "type": "base64",
+                                    "media_type": mediaType,
+                                    "data": base64Data
+                                ]
+                            ]
+                        }
+                        return nil
+                    }
+                    if !anthropicBlocks.isEmpty {
+                        conversationMessages.append(["role": role, "content": anthropicBlocks])
+                    }
+                } else {
+                    let content = (msg["content"] as? String ?? "").trimmingCharacters(in: .whitespacesAndNewlines)
+                    conversationMessages.append(["role": role, "content": content.isEmpty ? "[Image]" : content])
+                }
             }
         }
 
@@ -518,7 +552,9 @@ class AnthropicProvider: AIProvider {
 
             if hasAttachments, let attachments = msg.attachments {
                 var contentBlocks: [[String: Any]] = []
-                contentBlocks.append(["type": "text", "text": msg.content])
+                if !msg.content.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty {
+                    contentBlocks.append(["type": "text", "text": msg.content])
+                }
 
                 for attachment in attachments {
                     guard let data = attachment.data else { continue }
@@ -541,7 +577,8 @@ class AnthropicProvider: AIProvider {
                 }
                 apiMessages.append(["role": msg.role.rawValue, "content": contentBlocks])
             } else {
-                apiMessages.append(["role": msg.role.rawValue, "content": msg.content])
+                let content = msg.content.trimmingCharacters(in: .whitespacesAndNewlines)
+                apiMessages.append(["role": msg.role.rawValue, "content": content.isEmpty ? "[Image]" : content])
             }
         }
 

oAI/Services/BackupService.swift

@@ -0,0 +1,205 @@
+//
+//  BackupService.swift
+//  oAI
+//
+//  iCloud Drive backup of non-encrypted settings (Option C, v1)
+//
+// SPDX-License-Identifier: AGPL-3.0-or-later
+// Copyright (C) 2026 Rune Olsen
+//
+// This file is part of oAI.
+//
+// oAI is free software: you can redistribute it and/or modify
+// it under the terms of the GNU Affero General Public License as
+// published by the Free Software Foundation, either version 3 of the
+// License, or (at your option) any later version.
+//
+// oAI is distributed in the hope that it will be useful, but WITHOUT
+// ANY WARRANTY; without even the implied warranty of MERCHANTABILITY
+// or FITNESS FOR A PARTICULAR PURPOSE. See the GNU Affero General
+// Public License for more details.
+//
+// You should have received a copy of the GNU Affero General Public
+// License along with oAI. If not, see <https://www.gnu.org/licenses/>.
+
+import Foundation
+import os
+
+// MARK: - BackupManifest
+
+struct BackupManifest: Codable {
+    let version: Int
+    let createdAt: String
+    let appVersion: String
+    let credentialsIncluded: Bool
+    let settings: [String: String]
+    let credentials: [String: String]?
+}
+
+// MARK: - BackupService
+
+@Observable
+final class BackupService {
+    static let shared = BackupService()
+
+    private let log = Logger(subsystem: "oAI", category: "backup")
+
+    /// Whether iCloud Drive is available on this machine
+    var iCloudAvailable: Bool = false
+
+    /// Date of the last backup file on disk (from file attributes)
+    var lastBackupDate: Date?
+
+    /// URL of the last backup file
+    var lastBackupURL: URL?
+
+    // Keys excluded from backup — encrypted_ prefix + internal migration flags
+    private static let excludedKeys: Set<String> = [
+        "encrypted_openrouterAPIKey",
+        "encrypted_anthropicAPIKey",
+        "encrypted_openaiAPIKey",
+        "encrypted_googleAPIKey",
+        "encrypted_googleSearchEngineID",
+        "encrypted_anytypeMcpAPIKey",
+        "encrypted_paperlessAPIToken",
+        "encrypted_syncUsername",
+        "encrypted_syncPassword",
+        "encrypted_syncAccessToken",
+        "encrypted_emailUsername",
+        "encrypted_emailPassword",
+        "_migrated",
+        "_keychain_migrated",
+    ]
+
+    private init() {
+        checkForExistingBackup()
+    }
+
+    // MARK: - iCloud Path Resolution
+
+    private func resolveBackupDirectory() -> URL {
+        let home = FileManager.default.homeDirectoryForCurrentUser
+        let icloudRoot = home.appendingPathComponent("Library/Mobile Documents/com~apple~CloudDocs")
+        if FileManager.default.fileExists(atPath: icloudRoot.path) {
+            let icloudOAI = icloudRoot.appendingPathComponent("oAI")
+            try? FileManager.default.createDirectory(at: icloudOAI, withIntermediateDirectories: true)
+            return icloudOAI
+        }
+        // Fallback: Downloads
+        return FileManager.default.urls(for: .downloadsDirectory, in: .userDomainMask).first
+            ?? FileManager.default.temporaryDirectory
+    }
+
+    func checkForExistingBackup() {
+        let home = FileManager.default.homeDirectoryForCurrentUser
+        let icloudRoot = home.appendingPathComponent("Library/Mobile Documents/com~apple~CloudDocs")
+        iCloudAvailable = FileManager.default.fileExists(atPath: icloudRoot.path)
+
+        let dir = resolveBackupDirectory()
+        let fileURL = dir.appendingPathComponent("oai_backup.json")
+        if FileManager.default.fileExists(atPath: fileURL.path),
+           let attrs = try? FileManager.default.attributesOfItem(atPath: fileURL.path),
+           let modified = attrs[.modificationDate] as? Date {
+            lastBackupDate = modified
+            lastBackupURL = fileURL
+        }
+    }
+
+    // MARK: - Export
+
+    /// Export all non-encrypted settings to iCloud Drive (or Downloads).
+    /// Returns the URL where the file was written.
+    @discardableResult
+    func exportSettings() async throws -> URL {
+        // Load raw settings from DB
+        guard let allSettings = try? DatabaseService.shared.loadAllSettings() else {
+            throw BackupError.databaseReadFailed
+        }
+
+        // Filter out excluded keys
+        let filtered = allSettings.filter { !Self.excludedKeys.contains($0.key) }
+
+        // Build manifest
+        let formatter = ISO8601DateFormatter()
+        formatter.formatOptions = [.withInternetDateTime]
+        let manifest = BackupManifest(
+            version: 1,
+            createdAt: formatter.string(from: Date()),
+            appVersion: appVersion(),
+            credentialsIncluded: false,
+            settings: filtered,
+            credentials: nil
+        )
+
+        let encoder = JSONEncoder()
+        encoder.outputFormatting = [.prettyPrinted, .sortedKeys]
+        let data = try encoder.encode(manifest)
+
+        let dir = resolveBackupDirectory()
+        let fileURL = dir.appendingPathComponent("oai_backup.json")
+        try data.write(to: fileURL, options: .atomic)
+
+        log.info("Backup written to \(fileURL.path, privacy: .public) (\(filtered.count) settings)")
+
+        await MainActor.run {
+            self.lastBackupDate = Date()
+            self.lastBackupURL = fileURL
+        }
+
+        return fileURL
+    }
+
+    // MARK: - Import
+
+    /// Restore settings from a backup JSON file.
+    func importSettings(from url: URL) async throws {
+        let data = try Data(contentsOf: url)
+
+        let decoder = JSONDecoder()
+        let manifest: BackupManifest
+        do {
+            manifest = try decoder.decode(BackupManifest.self, from: data)
+        } catch {
+            throw BackupError.invalidFormat(error.localizedDescription)
+        }
+
+        guard manifest.version == 1 else {
+            throw BackupError.unsupportedVersion(manifest.version)
+        }
+
+        // Write each setting to the database
+        for (key, value) in manifest.settings {
+            DatabaseService.shared.setSetting(key: key, value: value)
+        }
+
+        // Refresh in-memory cache
+        SettingsService.shared.reloadFromDatabase()
+
+        log.info("Restored \(manifest.settings.count) settings from backup (v\(manifest.version))")
+    }
+
+    // MARK: - Helpers
+
+    private func appVersion() -> String {
+        Bundle.main.infoDictionary?["CFBundleShortVersionString"] as? String ?? "unknown"
+    }
+}
+
+// MARK: - BackupError
+
+enum BackupError: LocalizedError {
+    case databaseReadFailed
+    case invalidFormat(String)
+    case unsupportedVersion(Int)
+
+    var errorDescription: String? {
+        switch self {
+        case .databaseReadFailed:
+            return "Could not read settings from the database."
+        case .invalidFormat(let detail):
+            return "The backup file is not valid: \(detail)"
+        case .unsupportedVersion(let v):
+            return "Backup version \(v) is not supported by this version of oAI."
+        }
+    }
+}

oAI/Services/SettingsService.swift

@@ -953,6 +953,15 @@ class SettingsService {
         return true
     }
 
+    // MARK: - Cache Reload
+
+    /// Replace the in-memory cache with a fresh read from the database.
+    /// Called by BackupService after restoring a backup.
+    func reloadFromDatabase() {
+        cache = (try? DatabaseService.shared.loadAllSettings()) ?? [:]
+        Log.settings.info("Settings cache reloaded (\(self.cache.count) entries)")
+    }
+
     // MARK: - UserDefaults Migration
 
     private func migrateFromUserDefaultsIfNeeded() {

oAI/ViewModels/ChatViewModel.swift

@@ -295,6 +295,9 @@ Don't narrate future actions ("Let me...") - just use the tools.
     func sendMessage() {
         guard !inputText.trimmingCharacters(in: .whitespaces).isEmpty else { return }
 
+        // If already generating, cancel first — new message becomes a followup in context
+        if isGenerating { cancelGeneration() }
+
         let trimmedInput = inputText.trimmingCharacters(in: .whitespaces)
 
         // Handle slash escape: "//" becomes "/"
@@ -382,6 +385,11 @@ Don't narrate future actions ("Let me...") - just use the tools.
             MCPService.shared.resetBashSessionApproval()
             messages = loadedMessages
 
+            // Track identity so ⌘S can re-save under the same name
+            currentConversationId = conversation.id
+            currentConversationName = conversation.name
+            savedMessageCount = loadedMessages.filter { $0.role != .system }.count
+
             // Rebuild session stats from loaded messages
             for msg in loadedMessages {
                 sessionStats.addMessage(
@@ -1248,7 +1256,10 @@ Don't narrate future actions ("Let me...") - just use the tools.
                 var apiMessages: [[String: Any]] = [systemPrompt] + messagesToSend.map { msg in
                     let hasAttachments = msg.attachments?.contains(where: { $0.data != nil }) ?? false
                     if hasAttachments {
-                        var contentArray: [[String: Any]] = [["type": "text", "text": msg.content]]
+                        var contentArray: [[String: Any]] = []
+                        if !msg.content.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty {
+                            contentArray.append(["type": "text", "text": msg.content])
+                        }
                         for attachment in msg.attachments ?? [] {
                             guard let data = attachment.data else { continue }
                             switch attachment.type {
@@ -1264,7 +1275,8 @@ Don't narrate future actions ("Let me...") - just use the tools.
                         }
                         return ["role": msg.role.rawValue, "content": contentArray]
                     }
-                    return ["role": msg.role.rawValue, "content": msg.content]
+                    let content = msg.content.trimmingCharacters(in: .whitespacesAndNewlines)
+                    return ["role": msg.role.rawValue, "content": content.isEmpty ? "[Image]" : content]
                 }
 
                 // If this is a silent auto-continue, inject the prompt into the API call only
@@ -1311,7 +1323,13 @@ Don't narrate future actions ("Let me...") - just use the tools.
 
                     // Show what tools the model is calling
                     let toolNames = toolCalls.map { $0.functionName }.joined(separator: ", ")
-                    showSystemMessage("🔧 Calling: \(toolNames)")
+                    let toolMsgId = showSystemMessage("🔧 Calling: \(toolNames)")
+
+                    // Initialise detail entries with inputs (results fill in below)
+                    var toolDetails: [ToolCallDetail] = toolCalls.map { tc in
+                        ToolCallDetail(name: tc.functionName, input: tc.arguments, result: nil)
+                    }
+                    updateToolCallMessage(id: toolMsgId, details: toolDetails)
 
                     let usingTextCalls = !textCalls.isEmpty
 
@@ -1340,7 +1358,7 @@ Don't narrate future actions ("Let me...") - just use the tools.
 
                     // Execute each tool and append results
                     var toolResultLines: [String] = []
-                    for tc in toolCalls {
+                    for (i, tc) in toolCalls.enumerated() {
                         if Task.isCancelled {
                             wasCancelled = true
                             break
@@ -1362,6 +1380,10 @@ Don't narrate future actions ("Let me...") - just use the tools.
                             resultJSON = "{\"error\": \"Failed to serialize result\"}"
                         }
 
+                        // Update the detail entry with the result so the UI can show it
+                        toolDetails[i].result = resultJSON
+                        updateToolCallMessage(id: toolMsgId, details: toolDetails)
+
                         if usingTextCalls {
                             // Inject results as a user message for text-call models
                             toolResultLines.append("Tool result for \(tc.functionName):\n\(resultJSON)")
@@ -1462,7 +1484,8 @@ Don't narrate future actions ("Let me...") - just use the tools.
         }
     }
 
-    private func showSystemMessage(_ text: String) {
+    @discardableResult
+    private func showSystemMessage(_ text: String) -> UUID {
         let message = Message(
             role: .system,
             content: text,
@@ -1472,6 +1495,13 @@ Don't narrate future actions ("Let me...") - just use the tools.
             attachments: nil
         )
         messages.append(message)
+        return message.id
+    }
+
+    private func updateToolCallMessage(id: UUID, details: [ToolCallDetail]) {
+        if let idx = messages.firstIndex(where: { $0.id == id }) {
+            messages[idx].toolCalls = details
+        }
     }
     
     // MARK: - Error Helpers

oAI/Views/Main/FooterView.swift

@@ -87,7 +87,7 @@ struct FooterView: View {
 
             // Shortcuts hint
             #if os(macOS)
-            Text("⌘N New • ⌘M Model • ⌘⇧S Save")
+            Text("⌘N New • ⌘M Model • ⌘S Save")
                 .font(.caption2)
                 .foregroundColor(.oaiSecondary)
             #endif

oAI/Views/Main/MessageRow.swift

@@ -33,6 +33,8 @@ struct MessageRow: View {
     let viewModel: ChatViewModel?
     private let settings = SettingsService.shared
 
+    @State private var isExpanded = false
+
     #if os(macOS)
     @State private var isHovering = false
     @State private var showCopied = false
@@ -82,8 +84,8 @@ struct MessageRow: View {
                         .help("Star this message to always include it in context")
                     }
 
-                    // Copy button (assistant messages only, visible on hover)
-                    if message.role == .assistant && isHovering && !message.content.isEmpty {
+                    // Copy button (user + assistant messages, visible on hover)
+                    if (message.role == .assistant || message.role == .user) && isHovering && !message.content.isEmpty {
                         Button(action: copyContent) {
                             HStack(spacing: 3) {
                                 Image(systemName: showCopied ? "checkmark" : "doc.on.doc")
@@ -188,27 +190,126 @@ struct MessageRow: View {
 
     @ViewBuilder
     private var compactSystemMessage: some View {
-        HStack(spacing: 8) {
-            Image(systemName: "wrench.and.screwdriver")
-                .font(.system(size: 11))
-                .foregroundColor(.secondary)
+        let expandable = message.toolCalls != nil
+        VStack(alignment: .leading, spacing: 0) {
+            Button(action: {
+                if expandable {
+                    withAnimation(.easeInOut(duration: 0.18)) { isExpanded.toggle() }
+                }
+            }) {
+                HStack(spacing: 8) {
+                    Image(systemName: "wrench.and.screwdriver")
+                        .font(.system(size: 11))
+                        .foregroundColor(.secondary)
 
-            Text(message.content)
-                .font(.system(size: 11))
-                .foregroundColor(.secondary)
+                    Text(message.content)
+                        .font(.system(size: 11))
+                        .foregroundColor(.secondary)
 
-            Spacer()
+                    Spacer()
 
-            Text(message.timestamp, style: .time)
-                .font(.system(size: 10))
-                .foregroundColor(.secondary.opacity(0.7))
+                    if expandable {
+                        Image(systemName: isExpanded ? "chevron.up" : "chevron.down")
+                            .font(.system(size: 9, weight: .medium))
+                            .foregroundColor(.secondary.opacity(0.5))
+                    }
+
+                    Text(message.timestamp, style: .time)
+                        .font(.system(size: 10))
+                        .foregroundColor(.secondary.opacity(0.7))
+                }
+                .padding(.horizontal, 12)
+                .padding(.vertical, 6)
+                .contentShape(Rectangle())
+            }
+            .buttonStyle(.plain)
+
+            if isExpanded, let calls = message.toolCalls {
+                Divider()
+                    .padding(.horizontal, 8)
+                toolCallsDetailView(calls)
+            }
         }
-        .padding(.horizontal, 12)
-        .padding(.vertical, 6)
         .background(Color.secondary.opacity(0.08))
         .cornerRadius(6)
     }
 
+    @ViewBuilder
+    private func toolCallsDetailView(_ calls: [ToolCallDetail]) -> some View {
+        VStack(alignment: .leading, spacing: 0) {
+            ForEach(calls.indices, id: \.self) { i in
+                let call = calls[i]
+                VStack(alignment: .leading, spacing: 6) {
+                    // Tool name + status
+                    HStack(spacing: 6) {
+                        Image(systemName: "function")
+                            .font(.system(size: 10, weight: .semibold))
+                            .foregroundColor(.secondary)
+                        Text(call.name)
+                            .font(.system(size: 11, weight: .semibold))
+                            .foregroundColor(.secondary)
+                        Spacer()
+                        if call.result == nil {
+                            ProgressView()
+                                .scaleEffect(0.5)
+                                .frame(width: 12, height: 12)
+                        } else {
+                            Image(systemName: "checkmark.circle.fill")
+                                .font(.system(size: 10))
+                                .foregroundColor(.green.opacity(0.8))
+                        }
+                    }
+
+                    // Input
+                    if !call.input.isEmpty && call.input != "{}" {
+                        toolDetailSection(label: "Input", text: prettyJSON(call.input), maxHeight: 100)
+                    }
+
+                    // Result
+                    if let result = call.result {
+                        toolDetailSection(label: "Result", text: prettyJSON(result), maxHeight: 180)
+                    }
+                }
+                .padding(.horizontal, 12)
+                .padding(.vertical, 8)
+
+                if i < calls.count - 1 {
+                    Divider().padding(.horizontal, 12)
+                }
+            }
+        }
+    }
+
+    @ViewBuilder
+    private func toolDetailSection(label: String, text: String, maxHeight: CGFloat) -> some View {
+        VStack(alignment: .leading, spacing: 2) {
+            Text(label.uppercased())
+                .font(.system(size: 9, weight: .semibold))
+                .foregroundColor(.secondary.opacity(0.6))
+            ScrollView([.vertical, .horizontal]) {
+                Text(text)
+                    .font(.system(size: 10, design: .monospaced))
+                    .foregroundColor(.secondary)
+                    .textSelection(.enabled)
+                    .frame(maxWidth: .infinity, alignment: .leading)
+                    .fixedSize(horizontal: false, vertical: true)
+            }
+            .frame(maxHeight: maxHeight)
+            .background(Color.secondary.opacity(0.06))
+            .cornerRadius(4)
+        }
+    }
+
+    private func prettyJSON(_ raw: String) -> String {
+        guard let data = raw.data(using: .utf8),
+              let obj = try? JSONSerialization.jsonObject(with: data),
+              let pretty = try? JSONSerialization.data(withJSONObject: obj, options: [.prettyPrinted, .sortedKeys]),
+              let str = String(data: pretty, encoding: .utf8) else {
+            return raw
+        }
+        return str
+    }
+
     // MARK: - Message Content
 
     @ViewBuilder

oAI/Views/Screens/HelpView.swift

@@ -112,7 +112,8 @@ private let helpCategories: [CommandCategory] = [
             command: "/save <name>",
             brief: "Save current conversation",
             detail: "Saves all messages in the current session under the given name. You can load it later to continue the conversation.",
-            examples: ["/save my-project-chat", "/save debug session"]
+            examples: ["/save my-project-chat", "/save debug session"],
+            shortcut: "⌘S"
         ),
         CommandDetail(
             command: "/load",
@@ -191,7 +192,8 @@ private let helpCategories: [CommandCategory] = [
             command: "/stats",
             brief: "Show session statistics",
             detail: "Displays statistics for the current session: message count, total tokens used, estimated cost, and session duration.",
-            examples: ["/stats"]
+            examples: ["/stats"],
+            shortcut: "⌘⇧S"
         ),
     ]),
 ]

oAI/Views/Screens/SettingsView.swift

@@ -65,6 +65,14 @@ struct SettingsView: View {
     @State private var isTestingPaperless = false
     @State private var paperlessTestResult: String?
 
+    // Backup state
+    private let backupService = BackupService.shared
+    @State private var isExporting = false
+    @State private var isImporting = false
+    @State private var backupMessage: String?
+    @State private var backupMessageIsError = false
+    @State private var showRestoreFilePicker = false
+
     // Email handler state
     @State private var showEmailLog = false
     @State private var showEmailModelSelector = false
@@ -135,6 +143,7 @@ It's better to admit "I need more information" or "I cannot do that" than to fak
                 tabButton(4, icon: "arrow.triangle.2.circlepath", label: "Sync")
                 tabButton(5, icon: "envelope",                    label: "Email")
                 tabButton(8, icon: "doc.text",                    label: "Paperless")
+                tabButton(9, icon: "icloud.and.arrow.up",         label: "Backup")
             }
             .padding(.horizontal, 16)
             .padding(.bottom, 12)
@@ -162,6 +171,8 @@ It's better to admit "I need more information" or "I cannot do that" than to fak
                         agentSkillsTab
                     case 8:
                         paperlessTab
+                    case 9:
+                        backupTab
                     default:
                         generalTab
                     }
@@ -171,10 +182,24 @@ It's better to admit "I need more information" or "I cannot do that" than to fak
             }
 
         }
-        .frame(minWidth: 740, idealWidth: 820, minHeight: 620, idealHeight: 760)
+        .frame(minWidth: 860, idealWidth: 940, minHeight: 620, idealHeight: 760)
         .sheet(isPresented: $showEmailLog) {
             EmailLogView()
         }
+        .fileImporter(
+            isPresented: $showRestoreFilePicker,
+            allowedContentTypes: [.json],
+            allowsMultipleSelection: false
+        ) { result in
+            switch result {
+            case .success(let urls):
+                guard let url = urls.first else { return }
+                Task { await performRestore(from: url) }
+            case .failure(let error):
+                backupMessage = "Could not open file: \(error.localizedDescription)"
+                backupMessageIsError = true
+            }
+        }
     }
 
     // MARK: - General Tab
@@ -1823,6 +1848,184 @@ It's better to admit "I need more information" or "I cannot do that" than to fak
         }
     }
 
+    // MARK: - Backup Tab
+
+    @ViewBuilder
+    private var backupTab: some View {
+        VStack(alignment: .leading, spacing: 20) {
+            // Warning notice
+            VStack(alignment: .leading, spacing: 6) {
+                sectionHeader("iCloud Drive Backup")
+                HStack(alignment: .top, spacing: 8) {
+                    Image(systemName: "exclamationmark.triangle.fill")
+                        .foregroundStyle(.orange)
+                        .font(.system(size: 14))
+                    Text("API keys and credentials are **not** included in the backup. You will need to re-enter them after restoring on a new machine.")
+                        .font(.system(size: 13))
+                        .fixedSize(horizontal: false, vertical: true)
+                }
+                .padding(.horizontal, 4)
+                .padding(.top, 2)
+            }
+
+            // Status
+            VStack(alignment: .leading, spacing: 6) {
+                sectionHeader("Status")
+                formSection {
+                    row("iCloud Drive") {
+                        HStack(spacing: 6) {
+                            Circle()
+                                .fill(backupService.iCloudAvailable ? Color.green : Color.orange)
+                                .frame(width: 8, height: 8)
+                            Text(backupService.iCloudAvailable ? "Available" : "Not available — using Downloads")
+                                .font(.system(size: 13))
+                                .foregroundStyle(.secondary)
+                        }
+                    }
+                    rowDivider()
+                    row("Last Backup") {
+                        if let date = backupService.lastBackupDate {
+                            Text(formatBackupDate(date))
+                                .font(.system(size: 13))
+                                .foregroundStyle(.secondary)
+                        } else {
+                            Text("Never")
+                                .font(.system(size: 13))
+                                .foregroundStyle(.secondary)
+                        }
+                    }
+                }
+            }
+
+            // Actions
+            VStack(alignment: .leading, spacing: 6) {
+                sectionHeader("Actions")
+                formSection {
+                    HStack(spacing: 12) {
+                        Button(action: { Task { await performBackup() } }) {
+                            HStack(spacing: 6) {
+                                if isExporting {
+                                    ProgressView().scaleEffect(0.7).frame(width: 14, height: 14)
+                                } else {
+                                    Image(systemName: "icloud.and.arrow.up")
+                                }
+                                Text("Back Up Now")
+                            }
+                        }
+                        .disabled(isExporting || isImporting)
+
+                        Button(action: { showRestoreFilePicker = true }) {
+                            HStack(spacing: 6) {
+                                if isImporting {
+                                    ProgressView().scaleEffect(0.7).frame(width: 14, height: 14)
+                                } else {
+                                    Image(systemName: "icloud.and.arrow.down")
+                                }
+                                Text("Restore from File…")
+                            }
+                        }
+                        .disabled(isExporting || isImporting)
+
+                        Spacer()
+                    }
+                    .padding(.horizontal, 16)
+                    .padding(.vertical, 10)
+
+                    if let msg = backupMessage {
+                        rowDivider()
+                        HStack(spacing: 6) {
+                            Image(systemName: backupMessageIsError ? "xmark.circle.fill" : "checkmark.circle.fill")
+                                .foregroundStyle(backupMessageIsError ? .red : .green)
+                            Text(msg)
+                                .font(.system(size: 13))
+                                .foregroundStyle(backupMessageIsError ? .red : .primary)
+                                .fixedSize(horizontal: false, vertical: true)
+                        }
+                        .padding(.horizontal, 16)
+                        .padding(.vertical, 8)
+                    }
+                }
+            }
+
+            // Backup location
+            if let url = backupService.lastBackupURL {
+                VStack(alignment: .leading, spacing: 4) {
+                    Text("Backup location:")
+                        .font(.system(size: 13, weight: .medium))
+                    Text(url.path.replacingOccurrences(
+                        of: FileManager.default.homeDirectoryForCurrentUser.path,
+                        with: "~"))
+                        .font(.system(size: 12))
+                        .foregroundStyle(.secondary)
+                        .textSelection(.enabled)
+                }
+                .padding(.horizontal, 4)
+            }
+        }
+        .onAppear {
+            backupService.checkForExistingBackup()
+        }
+    }
+
+    private func performBackup() async {
+        await MainActor.run {
+            isExporting = true
+            backupMessage = nil
+        }
+        do {
+            let url = try await backupService.exportSettings()
+            let shortPath = url.path.replacingOccurrences(
+                of: FileManager.default.homeDirectoryForCurrentUser.path,
+                with: "~")
+            await MainActor.run {
+                backupMessage = "Backup saved to \(shortPath)"
+                backupMessageIsError = false
+                isExporting = false
+            }
+        } catch {
+            await MainActor.run {
+                backupMessage = error.localizedDescription
+                backupMessageIsError = true
+                isExporting = false
+            }
+        }
+    }
+
+    private func performRestore(from url: URL) async {
+        await MainActor.run {
+            isImporting = true
+            backupMessage = nil
+        }
+        do {
+            _ = url.startAccessingSecurityScopedResource()
+            defer { url.stopAccessingSecurityScopedResource() }
+            try await backupService.importSettings(from: url)
+            await MainActor.run {
+                backupMessage = "Settings restored. Re-enter your API keys to resume using oAI."
+                backupMessageIsError = false
+                isImporting = false
+            }
+        } catch {
+            await MainActor.run {
+                backupMessage = error.localizedDescription
+                backupMessageIsError = true
+                isImporting = false
+            }
+        }
+    }
+
+    private func formatBackupDate(_ date: Date) -> String {
+        let cal = Calendar.current
+        if cal.isDateInToday(date) {
+            let tf = DateFormatter()
+            tf.dateFormat = "HH:mm"
+            return "Today \(tf.string(from: date))"
+        }
+        let df = DateFormatter()
+        df.dateFormat = "dd.MM.yyyy HH:mm"
+        return df.string(from: date)
+    }
+
     // MARK: - Tab Navigation
 
     private func tabButton(_ tag: Int, icon: String, label: String) -> some View {
@@ -1856,6 +2059,7 @@ It's better to admit "I need more information" or "I cannot do that" than to fak
         case 6: return "Shortcuts"
         case 7: return "Skills"
         case 8: return "Paperless"
+        case 9: return "Backup"
         default: return "Settings"
         }
     }

oAI/oAIApp.swift

@@ -84,6 +84,9 @@ struct oAIApp: App {
             CommandGroup(replacing: .newItem) {
                 Button("New Chat") { chatViewModel.newConversation() }
                     .keyboardShortcut("n", modifiers: .command)
+                Button("Clear Chat") { chatViewModel.clearChat() }
+                    .keyboardShortcut("k", modifiers: .command)
+                    .disabled(chatViewModel.messages.filter { $0.role != .system }.isEmpty)
             }
 
             CommandGroup(after: .newItem) {
@@ -93,8 +96,10 @@ struct oAIApp: App {
 
             CommandGroup(replacing: .saveItem) {
                 Button("Save Chat") { chatViewModel.saveFromMenu() }
-                    .keyboardShortcut("s", modifiers: [.command, .shift])
+                    .keyboardShortcut("s", modifiers: .command)
                     .disabled(chatViewModel.messages.filter { $0.role != .system }.isEmpty)
+                Button("Stats") { chatViewModel.showStats = true }
+                    .keyboardShortcut("s", modifiers: [.command, .shift])
             }
 
             CommandGroup(after: .importExport) {