iCloud Backup, better chatview exp. bugfixes++

README.md

@@ -8,7 +8,7 @@ A powerful native macOS AI chat application with support for multiple providers,
 
 ### 🤖 Multi-Provider Support
 - **OpenAI** - GPT models with native API support
-- **Anthropic** - Claude models with OAuth integration
+- **Anthropic** - All Claude models
 - **OpenRouter** - Access to 300+ AI models from multiple providers
 - **Ollama** - Local model inference for privacy
 

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 = 2.3.1;
+				MARKETING_VERSION = 2.3.4;
 				PRODUCT_BUNDLE_IDENTIFIER = com.oai.oAI;
 				PRODUCT_NAME = "$(TARGET_NAME)";
 				REGISTER_APP_GROUPS = YES;
@@ -323,7 +323,7 @@
 				LD_RUNPATH_SEARCH_PATHS = "@executable_path/Frameworks";
 				"LD_RUNPATH_SEARCH_PATHS[sdk=macosx*]" = "@executable_path/../Frameworks";
 				MACOSX_DEPLOYMENT_TARGET = 26.2;
-				MARKETING_VERSION = 2.3.1;
+				MARKETING_VERSION = 2.3.4;
 				PRODUCT_BUNDLE_IDENTIFIER = com.oai.oAI;
 				PRODUCT_NAME = "$(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

@@ -73,7 +73,11 @@ class AnthropicProvider: AIProvider {
     // MARK: - Models
 
     /// Local metadata used to enrich API results (pricing, context length) and as offline fallback.
+    /// Entries are matched by exact ID first; if no exact match is found, the enrichment step
+    /// falls back to prefix matching so newly-released model variants (e.g. "claude-sonnet-4-6-20260301")
+    /// still inherit the correct pricing tier.
     private static let knownModels: [ModelInfo] = [
+        // Claude 4.x series
         ModelInfo(
             id: "claude-opus-4-6",
             name: "Claude Opus 4.6",
@@ -82,6 +86,31 @@ class AnthropicProvider: AIProvider {
             pricing: .init(prompt: 15.0, completion: 75.0),
             capabilities: .init(vision: true, tools: true, online: true)
         ),
+        ModelInfo(
+            id: "claude-sonnet-4-6",
+            name: "Claude Sonnet 4.6",
+            description: "Best balance of speed and capability",
+            contextLength: 200_000,
+            pricing: .init(prompt: 3.0, completion: 15.0),
+            capabilities: .init(vision: true, tools: true, online: true)
+        ),
+        ModelInfo(
+            id: "claude-haiku-4-6",
+            name: "Claude Haiku 4.6",
+            description: "Fastest and most affordable",
+            contextLength: 200_000,
+            pricing: .init(prompt: 0.80, completion: 4.0),
+            capabilities: .init(vision: true, tools: true, online: true)
+        ),
+        // Claude 4.5 series
+        ModelInfo(
+            id: "claude-opus-4-5",
+            name: "Claude Opus 4.5",
+            description: "Previous generation Opus",
+            contextLength: 200_000,
+            pricing: .init(prompt: 15.0, completion: 75.0),
+            capabilities: .init(vision: true, tools: true, online: true)
+        ),
         ModelInfo(
             id: "claude-opus-4-5-20251101",
             name: "Claude Opus 4.5",
@@ -90,6 +119,14 @@ class AnthropicProvider: AIProvider {
             pricing: .init(prompt: 15.0, completion: 75.0),
             capabilities: .init(vision: true, tools: true, online: true)
         ),
+        ModelInfo(
+            id: "claude-sonnet-4-5",
+            name: "Claude Sonnet 4.5",
+            description: "Best balance of speed and capability",
+            contextLength: 200_000,
+            pricing: .init(prompt: 3.0, completion: 15.0),
+            capabilities: .init(vision: true, tools: true, online: true)
+        ),
         ModelInfo(
             id: "claude-sonnet-4-5-20250929",
             name: "Claude Sonnet 4.5",
@@ -98,6 +135,14 @@ class AnthropicProvider: AIProvider {
             pricing: .init(prompt: 3.0, completion: 15.0),
             capabilities: .init(vision: true, tools: true, online: true)
         ),
+        ModelInfo(
+            id: "claude-haiku-4-5",
+            name: "Claude Haiku 4.5",
+            description: "Fastest and most affordable",
+            contextLength: 200_000,
+            pricing: .init(prompt: 0.80, completion: 4.0),
+            capabilities: .init(vision: true, tools: true, online: true)
+        ),
         ModelInfo(
             id: "claude-haiku-4-5-20251001",
             name: "Claude Haiku 4.5",
@@ -106,6 +151,7 @@ class AnthropicProvider: AIProvider {
             pricing: .init(prompt: 0.80, completion: 4.0),
             capabilities: .init(vision: true, tools: true, online: true)
         ),
+        // Claude 3.x series
         ModelInfo(
             id: "claude-3-7-sonnet-20250219",
             name: "Claude 3.7 Sonnet",
@@ -124,6 +170,14 @@ class AnthropicProvider: AIProvider {
         ),
     ]
 
+    /// Pricing tiers used for fuzzy fallback matching on unknown model IDs.
+    /// Keyed by model name prefix (longest match wins).
+    private static let pricingFallback: [(prefix: String, prompt: Double, completion: Double)] = [
+        ("claude-opus",   15.0, 75.0),
+        ("claude-sonnet",  3.0, 15.0),
+        ("claude-haiku",   0.80, 4.0),
+    ]
+
     /// Fetch live model list from GET /v1/models, enriched with local pricing/context metadata.
     /// Falls back to knownModels if the request fails (no key, offline, etc.).
     func listModels() async throws -> [ModelInfo] {
@@ -158,14 +212,20 @@ class AnthropicProvider: AIProvider {
                 guard let id = item["id"] as? String,
                       id.hasPrefix("claude-") else { return nil }
                 let displayName = item["display_name"] as? String ?? id
+                // Exact match first
                 if let known = enrichment[id] { return known }
-                // Unknown new model — use display name and sensible defaults
+                // Fuzzy fallback: find the longest prefix that matches
+                let fallback = Self.pricingFallback
+                    .filter { id.hasPrefix($0.prefix) }
+                    .max(by: { $0.prefix.count < $1.prefix.count })
+                let pricing = fallback.map { ModelInfo.Pricing(prompt: $0.prompt, completion: $0.completion) }
+                    ?? ModelInfo.Pricing(prompt: 0, completion: 0)
                 return ModelInfo(
                     id: id,
                     name: displayName,
                     description: item["description"] as? String ?? "",
                     contextLength: 200_000,
-                    pricing: .init(prompt: 0, completion: 0),
+                    pricing: pricing,
                     capabilities: .init(vision: true, tools: true, online: false)
                 )
             }
@@ -258,7 +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])
+                }
             }
         }
 
@@ -458,7 +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 }
@@ -481,7 +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/EmailHandlerService.swift

@@ -273,7 +273,7 @@ final class EmailHandlerService {
 
         ---
 
-        Please provide a complete, well-formatted response to this email. Your response will be sent as an HTML email.
+        Please provide a complete, well-formatted response to this email. Write the reply directly — do not wrap it in code fences or markdown blocks.
         """
 
         return prompt
@@ -299,7 +299,8 @@ final class EmailHandlerService {
         - Be professional and courteous
         - Keep responses concise and relevant
         - Use proper email etiquette
-        - Format your response using Markdown (it will be converted to HTML)
+        - Format your response using Markdown (bold, lists, headings are welcome)
+        - Do NOT wrap your response in code fences or ```html blocks — write the email body directly
         - If you need information from files, you have read-only access via MCP tools
         - Never claim to write, modify, or delete files (read-only access)
         - Sign emails appropriately
@@ -412,27 +413,46 @@ final class EmailHandlerService {
     }
 
     private func markdownToHTML(_ markdown: String) -> String {
-        // Basic markdown to HTML conversion
-        // TODO: Use proper markdown parser for production
-        var html = markdown
+        var text = markdown.trimmingCharacters(in: .whitespacesAndNewlines)
 
-        // Paragraphs
-        html = html.replacingOccurrences(of: "\n\n", with: "</p><p>")
-        html = "<p>\(html)</p>"
+        // Strip outer code fence wrapping the entire response
+        // Models sometimes wrap their reply in ```html ... ``` or ``` ... ```
+        let lines = text.components(separatedBy: "\n")
+        if lines.count >= 2 {
+            let first = lines[0].trimmingCharacters(in: .whitespaces)
+            let last = lines[lines.count - 1].trimmingCharacters(in: .whitespaces)
+            if (first == "```" || first.hasPrefix("```")) && last == "```" {
+                text = lines.dropFirst().dropLast().joined(separator: "\n")
+                    .trimmingCharacters(in: .whitespacesAndNewlines)
+            }
+        }
+
+        // Strip any remaining fenced code blocks (preserve content, remove fences)
+        text = text.replacingOccurrences(
+            of: #"```[a-z]*\n([\s\S]*?)```"#,
+            with: "$1",
+            options: .regularExpression
+        )
 
         // Bold
-        html = html.replacingOccurrences(of: #"\*\*(.+?)\*\*"#, with: "<strong>$1</strong>", options: .regularExpression)
+        text = text.replacingOccurrences(of: #"\*\*(.+?)\*\*"#, with: "<strong>$1</strong>", options: .regularExpression)
 
-        // Italic
-        html = html.replacingOccurrences(of: #"\*(.+?)\*"#, with: "<em>$1</em>", options: .regularExpression)
+        // Italic (avoid matching bold's leftover *)
+        text = text.replacingOccurrences(of: #"(?<!\*)\*(?!\*)(.+?)(?<!\*)\*(?!\*)"#, with: "<em>$1</em>", options: .regularExpression)
 
         // Inline code
-        html = html.replacingOccurrences(of: #"`(.+?)`"#, with: "<code>$1</code>", options: .regularExpression)
+        text = text.replacingOccurrences(of: #"`([^`\n]+)`"#, with: "<code>$1</code>", options: .regularExpression)
 
-        // Line breaks
-        html = html.replacingOccurrences(of: "\n", with: "<br>")
+        // Split into paragraphs on double newlines, wrap each in <p>
+        let paragraphs = text.components(separatedBy: "\n\n")
+            .map { $0.trimmingCharacters(in: .whitespacesAndNewlines) }
+            .filter { !$0.isEmpty }
+            .map { para in
+                let withBreaks = para.replacingOccurrences(of: "\n", with: "<br>")
+                return "<p>\(withBreaks)</p>"
+            }
 
-        return html
+        return paragraphs.joined(separator: "\n")
     }
 
     // MARK: - Error Handling

oAI/Services/MCPService.swift

@@ -110,10 +110,23 @@ class MCPService {
     var respectGitignore: Bool { settings.mcpRespectGitignore }
 
     private let anytypeService = AnytypeMCPService.shared
+    private let paperlessService = PaperlessService.shared
+
+    // MARK: - Bash Approval State
+
+    struct PendingBashCommand: Identifiable {
+        let id = UUID()
+        let command: String
+        let workingDirectory: String
+    }
+
+    private(set) var pendingBashCommand: PendingBashCommand? = nil
+    private var pendingBashContinuation: CheckedContinuation<[String: Any], Never>? = nil
+    private(set) var bashSessionApproved: Bool = false
 
     // MARK: - Tool Schema Generation
 
-    func getToolSchemas() -> [Tool] {
+    func getToolSchemas(onlineMode: Bool = false) -> [Tool] {
         var tools: [Tool] = [
             makeTool(
                 name: "read_file",
@@ -214,6 +227,39 @@ class MCPService {
             tools.append(contentsOf: anytypeService.getToolSchemas())
         }
 
+        // Add Paperless-NGX tools if enabled and configured
+        if settings.paperlessEnabled && settings.paperlessConfigured {
+            tools.append(contentsOf: paperlessService.getToolSchemas())
+        }
+
+        // Add bash_execute tool when bash is enabled
+        if settings.bashEnabled {
+            let workDir = settings.bashWorkingDirectory
+            let timeout = settings.bashTimeout
+            let approvalNote = settings.bashRequireApproval ? " User approval required before execution." : ""
+            tools.append(makeTool(
+                name: "bash_execute",
+                description: "Execute a shell command via /bin/zsh and return stdout/stderr. Working directory: \(workDir). Timeout: \(timeout)s.\(approvalNote)",
+                properties: [
+                    "command": prop("string", "The shell command to execute")
+                ],
+                required: ["command"]
+            ))
+        }
+
+        // Add web_search tool when online mode is active
+        // (OpenRouter handles search natively via :online model suffix, so excluded here)
+        if onlineMode {
+            tools.append(makeTool(
+                name: "web_search",
+                description: "Search the web for current information using DuckDuckGo. Use this when you need up-to-date information, news, or facts not in your training data. Formulate a concise, focused search query.",
+                properties: [
+                    "query": prop("string", "The search query to look up")
+                ],
+                required: ["query"]
+            ))
+        }
+
         return tools
     }
 
@@ -327,11 +373,41 @@ class MCPService {
             }
             return copyFile(source: source, destination: destination)
 
+        case "bash_execute":
+            guard settings.bashEnabled else {
+                return ["error": "Bash execution is disabled. Enable it in Settings > MCP."]
+            }
+            guard let command = args["command"] as? String, !command.isEmpty else {
+                return ["error": "Missing required parameter: command"]
+            }
+            let workDir = settings.bashWorkingDirectory
+            if settings.bashRequireApproval {
+                return await executeBashWithApproval(command: command, workingDirectory: workDir)
+            } else {
+                return await runBashCommand(command, workingDirectory: workDir)
+            }
+
+        case "web_search":
+            let query = args["query"] as? String ?? ""
+            guard !query.isEmpty else {
+                return ["error": "Missing required parameter: query"]
+            }
+            let results = await WebSearchService.shared.search(query: query)
+            if results.isEmpty {
+                return ["results": [], "message": "No results found for: \(query)"]
+            }
+            let mapped = results.map { ["title": $0.title, "url": $0.url, "snippet": $0.snippet] }
+            return ["results": mapped]
+
         default:
             // Route anytype_* tools to AnytypeMCPService
             if name.hasPrefix("anytype_") {
                 return await anytypeService.executeTool(name: name, arguments: arguments)
             }
+            // Route paperless_* tools to PaperlessService
+            if name.hasPrefix("paperless_") {
+                return await paperlessService.executeTool(name: name, arguments: arguments)
+            }
             return ["error": "Unknown tool: \(name)"]
         }
     }
@@ -671,6 +747,113 @@ class MCPService {
         return ["success": true, "source": resolvedSrc, "destination": resolvedDst]
     }
 
+    // MARK: - Bash Execution
+
+    private func executeBashWithApproval(command: String, workingDirectory: String) async -> [String: Any] {
+        // If the user already approved all commands for this session, skip the UI
+        if bashSessionApproved {
+            return await runBashCommand(command, workingDirectory: workingDirectory)
+        }
+        return await withCheckedContinuation { continuation in
+            DispatchQueue.main.async {
+                self.pendingBashCommand = PendingBashCommand(command: command, workingDirectory: workingDirectory)
+                self.pendingBashContinuation = continuation
+            }
+        }
+    }
+
+    func approvePendingBashCommand(forSession: Bool = false) {
+        guard let pending = pendingBashCommand, let cont = pendingBashContinuation else { return }
+        pendingBashCommand = nil
+        pendingBashContinuation = nil
+        if forSession {
+            bashSessionApproved = true
+        }
+        Task.detached(priority: .userInitiated) {
+            let result = await self.runBashCommand(pending.command, workingDirectory: pending.workingDirectory)
+            cont.resume(returning: result)
+        }
+    }
+
+    func denyPendingBashCommand() {
+        guard pendingBashCommand != nil else { return }
+        pendingBashCommand = nil
+        pendingBashContinuation?.resume(returning: ["error": "User denied command execution"])
+        pendingBashContinuation = nil
+    }
+
+    func resetBashSessionApproval() {
+        bashSessionApproved = false
+    }
+
+    private func runBashCommand(_ command: String, workingDirectory: String) async -> [String: Any] {
+        let timeoutSeconds = settings.bashTimeout
+        let workDir = ((workingDirectory as NSString).expandingTildeInPath as NSString).standardizingPath
+        Log.mcp.info("bash_execute: \(command)")
+
+        return await withCheckedContinuation { continuation in
+            DispatchQueue.global(qos: .userInitiated).async {
+                let process = Process()
+                process.executableURL = URL(fileURLWithPath: "/bin/zsh")
+                process.arguments = ["-c", command]
+
+                var isDir: ObjCBool = false
+                if FileManager.default.fileExists(atPath: workDir, isDirectory: &isDir), isDir.boolValue {
+                    process.currentDirectoryURL = URL(fileURLWithPath: workDir)
+                }
+
+                let stdoutPipe = Pipe()
+                let stderrPipe = Pipe()
+                process.standardOutput = stdoutPipe
+                process.standardError = stderrPipe
+
+                var timedOut = false
+                let timeoutItem = DispatchWorkItem {
+                    if process.isRunning {
+                        timedOut = true
+                        process.terminate()
+                    }
+                }
+                DispatchQueue.global().asyncAfter(deadline: .now() + .seconds(timeoutSeconds), execute: timeoutItem)
+
+                do {
+                    try process.run()
+                    process.waitUntilExit()
+                } catch {
+                    timeoutItem.cancel()
+                    Log.mcp.error("bash_execute failed to start: \(error.localizedDescription)")
+                    continuation.resume(returning: ["error": "Failed to run command: \(error.localizedDescription)"])
+                    return
+                }
+
+                timeoutItem.cancel()
+
+                let stdout = String(data: stdoutPipe.fileHandleForReading.readDataToEndOfFile(), encoding: .utf8) ?? ""
+                let stderr = String(data: stderrPipe.fileHandleForReading.readDataToEndOfFile(), encoding: .utf8) ?? ""
+                let exitCode = Int(process.terminationStatus)
+
+                Log.mcp.info("bash_execute exit=\(exitCode) stdout=\(stdout.count)b stderr=\(stderr.count)b timedOut=\(timedOut)")
+
+                var result: [String: Any] = ["exit_code": exitCode]
+                if !stdout.isEmpty {
+                    let maxOut = 20_000
+                    result["stdout"] = stdout.count > maxOut
+                        ? String(stdout.prefix(maxOut)) + "\n... (output truncated)"
+                        : stdout
+                }
+                if !stderr.isEmpty {
+                    result["stderr"] = String(stderr.prefix(5_000))
+                }
+                if timedOut {
+                    result["timed_out"] = true
+                    result["note"] = "Command terminated after \(timeoutSeconds)s timeout"
+                }
+
+                continuation.resume(returning: result)
+            }
+        }
+    }
+
     // MARK: - Gitignore Support
 
     /// Reload gitignore rules for all allowed folders

oAI/Services/PaperlessService.swift

@@ -0,0 +1,496 @@
+//
+//  PaperlessService.swift
+//  oAI
+//
+//  Paperless-NGX integration: search, read, and upload documents via REST API
+//
+// 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
+
+@Observable
+class PaperlessService {
+    static let shared = PaperlessService()
+
+    private let settings = SettingsService.shared
+    private let log = Logger(subsystem: "com.oai.oAI", category: "mcp")
+    private let readTimeout: TimeInterval = 15
+    private let uploadTimeout: TimeInterval = 60
+
+    private(set) var isConnected = false
+
+    // In-memory caches for ID → name resolution
+    private var tagCache: [Int: String] = [:]
+    private var correspondentCache: [Int: String] = [:]
+    private var documentTypeCache: [Int: String] = [:]
+
+    private init() {}
+
+    // MARK: - Connection Test
+
+    func testConnection() async -> Result<String, Error> {
+        do {
+            let result = try await request(endpoint: "/api/documents/", queryParams: ["page_size": "1"])
+            if let count = result["count"] as? Int {
+                isConnected = true
+                return .success("Connected (\(count) document\(count == 1 ? "" : "s"))")
+            } else {
+                isConnected = true
+                return .success("Connected to Paperless-NGX")
+            }
+        } catch {
+            isConnected = false
+            return .failure(error)
+        }
+    }
+
+    // MARK: - Tool Schemas
+
+    func getToolSchemas() -> [Tool] {
+        return [
+            makeTool(
+                name: "paperless_search",
+                description: "Search for documents in Paperless-NGX by title, content, tags, or any text. Returns document metadata and a preview of OCR-extracted content. Use this to find invoices, contracts, letters, or any stored document.",
+                properties: [
+                    "query": prop("string", "Search query — can be text from document content, title, correspondent name, or tag"),
+                    "page": prop("number", "Page number for pagination (default: 1, each page has 25 results)")
+                ],
+                required: ["query"]
+            ),
+            makeTool(
+                name: "paperless_get_document",
+                description: "Get the full details and complete OCR-extracted text content of a specific Paperless-NGX document by ID. Use after paperless_search to read the full text of a document.",
+                properties: [
+                    "document_id": prop("number", "The numeric ID of the document to retrieve")
+                ],
+                required: ["document_id"]
+            ),
+            makeTool(
+                name: "paperless_list_tags",
+                description: "List all tags defined in Paperless-NGX with their document counts.",
+                properties: [:],
+                required: []
+            ),
+            makeTool(
+                name: "paperless_list_correspondents",
+                description: "List all correspondents (senders/recipients) defined in Paperless-NGX with their document counts.",
+                properties: [:],
+                required: []
+            ),
+            makeTool(
+                name: "paperless_list_document_types",
+                description: "List all document types defined in Paperless-NGX with their document counts.",
+                properties: [:],
+                required: []
+            ),
+            makeTool(
+                name: "paperless_upload_document",
+                description: "Upload a local file to Paperless-NGX for OCR processing and storage. Supports PDF, PNG, JPEG, TIFF, and other image formats.",
+                properties: [
+                    "file_path": prop("string", "Absolute path to the local file to upload"),
+                    "title": prop("string", "Optional title for the document"),
+                    "tag_ids": prop("string", "Optional comma-separated tag IDs to assign (e.g. '1,3,7')")
+                ],
+                required: ["file_path"]
+            )
+        ]
+    }
+
+    // MARK: - Tool Execution
+
+    func executeTool(name: String, arguments: String) async -> [String: Any] {
+        log.info("Executing Paperless tool: \(name)")
+
+        guard let argData = arguments.data(using: .utf8),
+              let args = try? JSONSerialization.jsonObject(with: argData) as? [String: Any] else {
+            return ["error": "Invalid arguments JSON"]
+        }
+
+        do {
+            switch name {
+            case "paperless_search":
+                guard let query = args["query"] as? String else {
+                    return ["error": "Missing required parameter: query"]
+                }
+                let page: Int
+                if let p = args["page"] as? Int { page = p }
+                else if let p = args["page"] as? Double { page = Int(p) }
+                else { page = 1 }
+                return try await searchDocuments(query: query, page: page)
+
+            case "paperless_get_document":
+                let docId: Int
+                if let id = args["document_id"] as? Int { docId = id }
+                else if let id = args["document_id"] as? Double { docId = Int(id) }
+                else { return ["error": "Missing or invalid parameter: document_id (expected integer)"] }
+                return try await getDocument(id: docId)
+
+            case "paperless_list_tags":
+                return try await listTags()
+
+            case "paperless_list_correspondents":
+                return try await listCorrespondents()
+
+            case "paperless_list_document_types":
+                return try await listDocumentTypes()
+
+            case "paperless_upload_document":
+                guard let filePath = args["file_path"] as? String else {
+                    return ["error": "Missing required parameter: file_path"]
+                }
+                let title = args["title"] as? String
+                let tagIds = args["tag_ids"] as? String
+                return try await uploadDocument(filePath: filePath, title: title, tagIds: tagIds)
+
+            default:
+                return ["error": "Unknown Paperless tool: \(name)"]
+            }
+        } catch PaperlessError.notConfigured {
+            return ["error": "Paperless-NGX is not configured. Set your URL and API token in Settings > Paperless."]
+        } catch PaperlessError.unauthorized {
+            return ["error": "Invalid API token. Check your Paperless-NGX token in Settings > Paperless."]
+        } catch PaperlessError.httpError(let code, let msg) {
+            return ["error": "Paperless-NGX API error \(code): \(msg)"]
+        } catch {
+            return ["error": "Paperless error: \(error.localizedDescription)"]
+        }
+    }
+
+    // MARK: - API Operations
+
+    private func searchDocuments(query: String, page: Int) async throws -> [String: Any] {
+        await prefetchCaches()
+
+        let result = try await request(endpoint: "/api/documents/", queryParams: [
+            "query": query,
+            "page": String(page)
+        ])
+
+        let total = result["count"] as? Int ?? 0
+        guard let rawResults = result["results"] as? [[String: Any]] else {
+            return ["total": total, "page": page, "results": []]
+        }
+
+        let formatted = rawResults.map { doc -> [String: Any] in
+            var item: [String: Any] = [:]
+            item["id"] = doc["id"] ?? 0
+            item["title"] = doc["title"] ?? "Untitled"
+            item["created"] = (doc["created"] as? String).map { String($0.prefix(10)) } ?? ""
+
+            if let corrId = doc["correspondent"] as? Int {
+                item["correspondent"] = correspondentCache[corrId] ?? "ID:\(corrId)"
+            }
+
+            if let dtId = doc["document_type"] as? Int {
+                item["document_type"] = documentTypeCache[dtId] ?? "ID:\(dtId)"
+            }
+
+            if let tagIds = doc["tags"] as? [Int] {
+                item["tags"] = tagIds.map { tagCache[$0] ?? "ID:\($0)" }
+            }
+
+            // Content preview capped at 500 chars
+            if let content = doc["content"] as? String, !content.isEmpty {
+                let preview = content.trimmingCharacters(in: .whitespacesAndNewlines)
+                item["content_preview"] = String(preview.prefix(500))
+            }
+
+            return item
+        }
+
+        return ["total": total, "page": page, "results": formatted]
+    }
+
+    private func getDocument(id: Int) async throws -> [String: Any] {
+        await prefetchCaches()
+
+        let doc = try await request(endpoint: "/api/documents/\(id)/")
+
+        var result: [String: Any] = [:]
+        result["id"] = doc["id"] ?? id
+        result["title"] = doc["title"] ?? "Untitled"
+        result["created"] = (doc["created"] as? String).map { String($0.prefix(10)) } ?? ""
+        result["added"] = (doc["added"] as? String).map { String($0.prefix(10)) } ?? ""
+        result["modified"] = (doc["modified"] as? String).map { String($0.prefix(10)) } ?? ""
+
+        if let corrId = doc["correspondent"] as? Int {
+            result["correspondent"] = correspondentCache[corrId] ?? "ID:\(corrId)"
+        }
+        if let dtId = doc["document_type"] as? Int {
+            result["document_type"] = documentTypeCache[dtId] ?? "ID:\(dtId)"
+        }
+        if let tagIds = doc["tags"] as? [Int] {
+            result["tags"] = tagIds.map { tagCache[$0] ?? "ID:\($0)" }
+        }
+        if let asn = doc["archive_serial_number"] as? String {
+            result["archive_serial_number"] = asn
+        }
+
+        // Full OCR content capped at 30,000 chars
+        if let content = doc["content"] as? String {
+            let trimmed = content.trimmingCharacters(in: .whitespacesAndNewlines)
+            result["content"] = String(trimmed.prefix(30_000))
+            result["content_length"] = trimmed.count
+        }
+
+        return result
+    }
+
+    private func listTags() async throws -> [String: Any] {
+        let result = try await request(endpoint: "/api/tags/", queryParams: ["page_size": "250"])
+        guard let items = result["results"] as? [[String: Any]] else {
+            return ["count": 0, "tags": []]
+        }
+        let formatted = items.map { tag -> [String: Any] in
+            ["id": tag["id"] ?? 0, "name": tag["name"] ?? "Unknown", "count": tag["document_count"] ?? 0]
+        }
+        return ["count": formatted.count, "tags": formatted]
+    }
+
+    private func listCorrespondents() async throws -> [String: Any] {
+        let result = try await request(endpoint: "/api/correspondents/", queryParams: ["page_size": "250"])
+        guard let items = result["results"] as? [[String: Any]] else {
+            return ["count": 0, "correspondents": []]
+        }
+        let formatted = items.map { c -> [String: Any] in
+            ["id": c["id"] ?? 0, "name": c["name"] ?? "Unknown", "count": c["document_count"] ?? 0]
+        }
+        return ["count": formatted.count, "correspondents": formatted]
+    }
+
+    private func listDocumentTypes() async throws -> [String: Any] {
+        let result = try await request(endpoint: "/api/document_types/", queryParams: ["page_size": "250"])
+        guard let items = result["results"] as? [[String: Any]] else {
+            return ["count": 0, "document_types": []]
+        }
+        let formatted = items.map { dt -> [String: Any] in
+            ["id": dt["id"] ?? 0, "name": dt["name"] ?? "Unknown", "count": dt["document_count"] ?? 0]
+        }
+        return ["count": formatted.count, "document_types": formatted]
+    }
+
+    private func uploadDocument(filePath: String, title: String?, tagIds: String?) async throws -> [String: Any] {
+        let expanded = (filePath as NSString).expandingTildeInPath
+        let resolved = (expanded as NSString).standardizingPath
+
+        guard FileManager.default.fileExists(atPath: resolved) else {
+            return ["error": "File not found: \(filePath)"]
+        }
+        guard let fileData = FileManager.default.contents(atPath: resolved) else {
+            return ["error": "Cannot read file: \(filePath)"]
+        }
+
+        let fileName = (resolved as NSString).lastPathComponent
+
+        guard let token = settings.paperlessAPIToken, !token.isEmpty else {
+            throw PaperlessError.notConfigured
+        }
+        let baseURL = settings.paperlessURL
+        guard !baseURL.isEmpty, let url = URL(string: baseURL + "/api/documents/post_document/") else {
+            throw PaperlessError.notConfigured
+        }
+
+        let boundary = "PaperlessBoundary\(UUID().uuidString.replacingOccurrences(of: "-", with: ""))"
+        var body = Data()
+
+        func appendField(_ name: String, _ value: String) {
+            body.append("--\(boundary)\r\n".data(using: .utf8)!)
+            body.append("Content-Disposition: form-data; name=\"\(name)\"\r\n\r\n".data(using: .utf8)!)
+            body.append("\(value)\r\n".data(using: .utf8)!)
+        }
+
+        if let title = title, !title.isEmpty {
+            appendField("title", title)
+        }
+
+        if let tagIds = tagIds {
+            let ids = tagIds.split(separator: ",").compactMap { Int($0.trimmingCharacters(in: .whitespaces)) }
+            for id in ids {
+                appendField("tags", String(id))
+            }
+        }
+
+        let mimeType = mimeTypeFor(fileName: fileName)
+        body.append("--\(boundary)\r\n".data(using: .utf8)!)
+        body.append("Content-Disposition: form-data; name=\"document\"; filename=\"\(fileName)\"\r\n".data(using: .utf8)!)
+        body.append("Content-Type: \(mimeType)\r\n\r\n".data(using: .utf8)!)
+        body.append(fileData)
+        body.append("\r\n--\(boundary)--\r\n".data(using: .utf8)!)
+
+        var urlRequest = URLRequest(url: url, timeoutInterval: uploadTimeout)
+        urlRequest.httpMethod = "POST"
+        urlRequest.setValue("Token \(token)", forHTTPHeaderField: "Authorization")
+        urlRequest.setValue("multipart/form-data; boundary=\(boundary)", forHTTPHeaderField: "Content-Type")
+        urlRequest.httpBody = body
+
+        let (data, response) = try await URLSession.shared.data(for: urlRequest)
+        guard let httpResponse = response as? HTTPURLResponse else {
+            throw PaperlessError.httpError(0, "Invalid response")
+        }
+
+        if httpResponse.statusCode == 401 { throw PaperlessError.unauthorized }
+
+        if (200...299).contains(httpResponse.statusCode) {
+            return ["success": true, "message": "Document uploaded successfully. Paperless-NGX will process it shortly."]
+        }
+
+        let msg = String(data: data, encoding: .utf8) ?? "Unknown error"
+        throw PaperlessError.httpError(httpResponse.statusCode, msg)
+    }
+
+    // MARK: - Cache Prefetch
+
+    private func prefetchCaches() async {
+        if tagCache.isEmpty {
+            if let result = try? await request(endpoint: "/api/tags/", queryParams: ["page_size": "250"]),
+               let items = result["results"] as? [[String: Any]] {
+                for item in items {
+                    if let id = item["id"] as? Int, let name = item["name"] as? String {
+                        tagCache[id] = name
+                    }
+                }
+            }
+        }
+        if correspondentCache.isEmpty {
+            if let result = try? await request(endpoint: "/api/correspondents/", queryParams: ["page_size": "250"]),
+               let items = result["results"] as? [[String: Any]] {
+                for item in items {
+                    if let id = item["id"] as? Int, let name = item["name"] as? String {
+                        correspondentCache[id] = name
+                    }
+                }
+            }
+        }
+        if documentTypeCache.isEmpty {
+            if let result = try? await request(endpoint: "/api/document_types/", queryParams: ["page_size": "250"]),
+               let items = result["results"] as? [[String: Any]] {
+                for item in items {
+                    if let id = item["id"] as? Int, let name = item["name"] as? String {
+                        documentTypeCache[id] = name
+                    }
+                }
+            }
+        }
+    }
+
+    // MARK: - HTTP Client
+
+    private func request(endpoint: String, queryParams: [String: String] = [:]) async throws -> [String: Any] {
+        guard let token = settings.paperlessAPIToken, !token.isEmpty else {
+            throw PaperlessError.notConfigured
+        }
+        let baseURL = settings.paperlessURL
+        guard !baseURL.isEmpty else { throw PaperlessError.notConfigured }
+
+        var urlString = baseURL + endpoint
+        if !queryParams.isEmpty {
+            var comps = URLComponents(string: urlString) ?? URLComponents()
+            comps.queryItems = queryParams.map { URLQueryItem(name: $0.key, value: $0.value) }
+            urlString = comps.url?.absoluteString ?? urlString
+        }
+
+        guard let url = URL(string: urlString) else {
+            throw PaperlessError.httpError(0, "Invalid URL: \(urlString)")
+        }
+
+        var urlRequest = URLRequest(url: url, timeoutInterval: readTimeout)
+        urlRequest.httpMethod = "GET"
+        urlRequest.setValue("Token \(token)", forHTTPHeaderField: "Authorization")
+        urlRequest.setValue("application/json", forHTTPHeaderField: "Accept")
+
+        do {
+            let (data, response) = try await URLSession.shared.data(for: urlRequest)
+
+            guard let httpResponse = response as? HTTPURLResponse else {
+                throw PaperlessError.httpError(0, "Invalid response")
+            }
+
+            if httpResponse.statusCode == 401 { throw PaperlessError.unauthorized }
+
+            guard (200...299).contains(httpResponse.statusCode) else {
+                let msg = String(data: data, encoding: .utf8) ?? "Unknown error"
+                throw PaperlessError.httpError(httpResponse.statusCode, msg)
+            }
+
+            guard let json = try? JSONSerialization.jsonObject(with: data) as? [String: Any] else {
+                return [:]
+            }
+            return json
+        } catch let error as PaperlessError {
+            throw error
+        } catch {
+            throw PaperlessError.httpError(0, error.localizedDescription)
+        }
+    }
+
+    // MARK: - Helpers
+
+    private func mimeTypeFor(fileName: String) -> String {
+        let ext = (fileName as NSString).pathExtension.lowercased()
+        switch ext {
+        case "pdf": return "application/pdf"
+        case "png": return "image/png"
+        case "jpg", "jpeg": return "image/jpeg"
+        case "tiff", "tif": return "image/tiff"
+        case "gif": return "image/gif"
+        case "webp": return "image/webp"
+        default: return "application/octet-stream"
+        }
+    }
+
+    private func makeTool(name: String, description: String, properties: [String: Tool.Function.Parameters.Property], required: [String]) -> Tool {
+        Tool(
+            type: "function",
+            function: Tool.Function(
+                name: name,
+                description: description,
+                parameters: Tool.Function.Parameters(
+                    type: "object",
+                    properties: properties,
+                    required: required
+                )
+            )
+        )
+    }
+
+    private func prop(_ type: String, _ description: String) -> Tool.Function.Parameters.Property {
+        Tool.Function.Parameters.Property(type: type, description: description, enum: nil)
+    }
+}
+
+// MARK: - Error Types
+
+enum PaperlessError: LocalizedError {
+    case notConfigured
+    case unauthorized
+    case httpError(Int, String)
+
+    var errorDescription: String? {
+        switch self {
+        case .notConfigured:
+            return "Paperless-NGX is not configured. Set your URL and API token in Settings > Paperless."
+        case .unauthorized:
+            return "Invalid API token. Check your Paperless-NGX token in Settings > Paperless."
+        case .httpError(let code, let msg):
+            return "Paperless-NGX API error \(code): \(msg)"
+        }
+    }
+}

oAI/Services/SettingsService.swift

@@ -42,6 +42,7 @@ class SettingsService {
         static let googleAPIKey = "googleAPIKey"
         static let googleSearchEngineID = "googleSearchEngineID"
         static let anytypeMcpAPIKey = "anytypeMcpAPIKey"
+        static let paperlessAPIToken = "paperlessAPIToken"
     }
 
     // Old keychain keys (for migration only)
@@ -446,6 +447,83 @@ class SettingsService {
         return !key.isEmpty
     }
 
+    // MARK: - Bash Execution Settings
+
+    var bashEnabled: Bool {
+        get { cache["bashEnabled"] == "true" }
+        set {
+            cache["bashEnabled"] = String(newValue)
+            DatabaseService.shared.setSetting(key: "bashEnabled", value: String(newValue))
+        }
+    }
+
+    var bashRequireApproval: Bool {
+        get { cache["bashRequireApproval"].map { $0 == "true" } ?? true }
+        set {
+            cache["bashRequireApproval"] = String(newValue)
+            DatabaseService.shared.setSetting(key: "bashRequireApproval", value: String(newValue))
+        }
+    }
+
+    var bashWorkingDirectory: String {
+        get { cache["bashWorkingDirectory"] ?? "~" }
+        set {
+            cache["bashWorkingDirectory"] = newValue
+            DatabaseService.shared.setSetting(key: "bashWorkingDirectory", value: newValue)
+        }
+    }
+
+    var bashTimeout: Int {
+        get { cache["bashTimeout"].flatMap(Int.init) ?? 30 }
+        set {
+            cache["bashTimeout"] = String(newValue)
+            DatabaseService.shared.setSetting(key: "bashTimeout", value: String(newValue))
+        }
+    }
+
+    // MARK: - Paperless-NGX Settings
+
+    var paperlessEnabled: Bool {
+        get { cache["paperlessEnabled"] == "true" }
+        set {
+            cache["paperlessEnabled"] = String(newValue)
+            DatabaseService.shared.setSetting(key: "paperlessEnabled", value: String(newValue))
+        }
+    }
+
+    var paperlessURL: String {
+        get { cache["paperlessURL"] ?? "" }
+        set {
+            var trimmed = newValue.trimmingCharacters(in: .whitespaces)
+            // Remove trailing slash for consistency
+            while trimmed.hasSuffix("/") { trimmed = String(trimmed.dropLast()) }
+            if trimmed.isEmpty {
+                cache.removeValue(forKey: "paperlessURL")
+                DatabaseService.shared.deleteSetting(key: "paperlessURL")
+            } else {
+                cache["paperlessURL"] = trimmed
+                DatabaseService.shared.setSetting(key: "paperlessURL", value: trimmed)
+            }
+        }
+    }
+
+    var paperlessAPIToken: String? {
+        get { try? DatabaseService.shared.getEncryptedSetting(key: EncryptedKeys.paperlessAPIToken) }
+        set {
+            if let value = newValue, !value.isEmpty {
+                try? DatabaseService.shared.setEncryptedSetting(key: EncryptedKeys.paperlessAPIToken, value: value)
+            } else {
+                DatabaseService.shared.deleteEncryptedSetting(key: EncryptedKeys.paperlessAPIToken)
+            }
+        }
+    }
+
+    var paperlessConfigured: Bool {
+        guard !paperlessURL.isEmpty else { return false }
+        guard let token = paperlessAPIToken else { return false }
+        return !token.isEmpty
+    }
+
     // MARK: - Search Settings
 
     var searchProvider: Settings.SearchProvider {
@@ -875,6 +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/Services/UpdateCheckService.swift

@@ -36,37 +36,44 @@ final class UpdateCheckService {
     var updateAvailable: Bool = false
     var latestVersion: String? = nil
 
-    private let apiURL = "https://gitlab.pm/api/v4/projects/rune%2Foai-swift/releases"
+    private let apiURL = "https://gitlab.pm/api/v1/repos/rune/oai-swift/releases/latest"
     private let releasesURL = URL(string: "https://gitlab.pm/rune/oai-swift/releases")!
 
     private init() {}
 
     /// Kick off a background update check. Silently does nothing on failure.
     func checkForUpdates() {
-        Task {
-            await performCheck()
+        Task.detached(priority: .background) {
+            await self.performCheck()
         }
     }
 
-    @MainActor
     private func performCheck() async {
         guard let url = URL(string: apiURL) else { return }
 
         var request = URLRequest(url: url)
         request.timeoutInterval = 10
 
-        guard let (data, _) = try? await URLSession.shared.data(for: request) else { return }
-        guard let releases = try? JSONSerialization.jsonObject(with: data) as? [[String: Any]],
-              let latest = releases.first,
-              let tagName = latest["tag_name"] as? String else { return }
+        guard let (data, _) = try? await URLSession.shared.data(for: request) else {
+            Log.ui.warning("UpdateCheck: network request failed")
+            return
+        }
+
+        guard let release = try? JSONSerialization.jsonObject(with: data) as? [String: Any],
+              let tagName = release["tag_name"] as? String else {
+            Log.ui.warning("UpdateCheck: unexpected API response — \(String(data: data, encoding: .utf8) ?? "<binary>")")
+            return
+        }
 
         // Strip leading "v" from tag (e.g. "v2.3.1" → "2.3.1")
         let latestVer = tagName.hasPrefix("v") ? String(tagName.dropFirst()) : tagName
         let currentVer = Bundle.main.infoDictionary?["CFBundleShortVersionString"] as? String ?? "0.0.0"
 
         if isNewer(latestVer, than: currentVer) {
-            self.latestVersion = latestVer
-            self.updateAvailable = true
+            await MainActor.run {
+                self.latestVersion = latestVer
+                self.updateAvailable = true
+            }
         }
     }
 

oAI/ViewModels/ChatViewModel.swift

@@ -56,7 +56,7 @@ class ChatViewModel {
     var modelInfoTarget: ModelInfo? = nil
     var commandHistory: [String] = []
     var historyIndex: Int = 0
-    var isAutoContinuing: Bool = false
+    private var silentContinuePrompt: String? = nil
 
     // Save tracking
     var currentConversationId: UUID? = nil
@@ -67,7 +67,6 @@ class ChatViewModel {
         let chatCount = messages.filter { $0.role != .system }.count
         return chatCount > 0 && chatCount != savedMessageCount
     }
-    var autoContinueCountdown: Int = 0
 
     // MARK: - Auto-Save Tracking
 
@@ -78,7 +77,6 @@ class ChatViewModel {
     // MARK: - Private State
 
     private var streamingTask: Task<Void, Never>?
-    private var autoContinueTask: Task<Void, Never>?
     private let settings = SettingsService.shared
     private let providerRegistry = ProviderRegistry.shared
 
@@ -164,6 +162,13 @@ Don't narrate future actions ("Let me...") - just use the tools.
         // Otherwise, build the prompt: default + conditional sections + custom (if append mode)
         var prompt = defaultSystemPrompt
 
+        // Prepend model identity to prevent models trained on Claude data from misidentifying themselves.
+        // Skip for direct Anthropic/OpenAI providers — those models know who they are.
+        if let model = selectedModel,
+           currentProvider != .anthropic && currentProvider != .openai {
+            prompt = "You are \(model.name).\n\n" + prompt
+        }
+
         // Add tool-specific guidelines if MCP is enabled (tools are available)
         if mcpEnabled {
             prompt += toolUsageGuidelines
@@ -290,6 +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 "/"
@@ -347,59 +355,21 @@ Don't narrate future actions ("Let me...") - just use the tools.
         streamingTask?.cancel()
         streamingTask = nil
         isGenerating = false
-        cancelAutoContinue()  // Also cancel any pending auto-continue
+        silentContinuePrompt = nil
     }
 
     func startAutoContinue() {
-        isAutoContinuing = true
-        autoContinueCountdown = 5
-
-        autoContinueTask = Task { @MainActor in
-            // Countdown from 5 to 1
-            for i in (1...5).reversed() {
-                if Task.isCancelled {
-                    isAutoContinuing = false
-                    return
-                }
-                autoContinueCountdown = i
-                try? await Task.sleep(for: .seconds(1))
-            }
-
-            // Continue the task
-            isAutoContinuing = false
-            autoContinueCountdown = 0
-
-            let continuePrompt = "Please continue from where you left off."
-
-            // Add user message
-            let userMessage = Message(
-                role: .user,
-                content: continuePrompt,
-                tokens: nil,
-                cost: nil,
-                timestamp: Date(),
-                attachments: nil,
-                responseTime: nil,
-                wasInterrupted: false,
-                modelId: selectedModel?.id
-            )
-            messages.append(userMessage)
-
-            // Continue generation
-            generateAIResponse(to: continuePrompt, attachments: nil)
+        showSystemMessage("↩ Continuing…")
+        silentContinuePrompt = "Please continue from where you left off."
+        Task { @MainActor in
+            generateAIResponse(to: "", attachments: nil)
         }
     }
 
-    func cancelAutoContinue() {
-        autoContinueTask?.cancel()
-        autoContinueTask = nil
-        isAutoContinuing = false
-        autoContinueCountdown = 0
-    }
-
     func clearChat() {
         messages.removeAll()
         sessionStats.reset()
+        MCPService.shared.resetBashSessionApproval()
         showSystemMessage("Chat cleared")
     }
 
@@ -412,8 +382,14 @@ Don't narrate future actions ("Let me...") - just use the tools.
 
             messages.removeAll()
             sessionStats.reset()
+            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(
@@ -435,6 +411,17 @@ Don't narrate future actions ("Let me...") - just use the tools.
     }
 
     /// Infer which provider owns a given model ID based on naming conventions.
+    /// Update the selected model and keep currentProvider + settings in sync.
+    /// Call this whenever the user picks a model in the model selector.
+    func selectModel(_ model: ModelInfo) {
+        let newProvider = inferProvider(from: model.id) ?? currentProvider
+        selectedModel = model
+        currentProvider = newProvider
+        settings.defaultModel = model.id
+        settings.defaultProvider = newProvider
+        MCPService.shared.resetBashSessionApproval()
+    }
+
     private func inferProvider(from modelId: String) -> Settings.Provider? {
         // OpenRouter models always contain a "/" (e.g. "anthropic/claude-3-5-sonnet")
         if modelId.contains("/") { return .openrouter }
@@ -767,8 +754,9 @@ Don't narrate future actions ("Let me...") - just use the tools.
         let mcp = MCPService.shared
         let mcpActive = mcpEnabled || settings.mcpEnabled
         let anytypeActive = settings.anytypeMcpEnabled && settings.anytypeMcpConfigured
+        let bashActive = settings.bashEnabled
         let modelSupportTools = selectedModel?.capabilities.tools ?? false
-        if modelSupportTools && (anytypeActive || (mcpActive && !mcp.allowedFolders.isEmpty)) {
+        if modelSupportTools && (anytypeActive || bashActive || (mcpActive && !mcp.allowedFolders.isEmpty)) {
             generateAIResponseWithTools(provider: provider, modelId: modelId)
             return
         }
@@ -881,7 +869,7 @@ Don't narrate future actions ("Let me...") - just use the tools.
                         temperature: chatRequest.temperature,
                         imageGeneration: true
                     )
-                    let response = try await provider.chat(request: nonStreamRequest)
+                    let response = try await withOverloadedRetry { try await provider.chat(request: nonStreamRequest) }
                     let responseTime = Date().timeIntervalSince(startTime)
 
                     if let index = messages.firstIndex(where: { $0.id == messageId }) {
@@ -1220,7 +1208,8 @@ Don't narrate future actions ("Let me...") - just use the tools.
             let startTime = Date()
             var wasCancelled = false
             do {
-                let tools = mcp.getToolSchemas()
+                // Include web_search tool when online mode is on (not needed for OpenRouter — it handles search via :online suffix)
+                let tools = mcp.getToolSchemas(onlineMode: onlineMode && currentProvider != .openrouter)
 
                 // Apply :online suffix for OpenRouter when online mode is active
                 var effectiveModelId = modelId
@@ -1259,20 +1248,6 @@ Don't narrate future actions ("Let me...") - just use the tools.
                     ? messages.filter { $0.role != .system }
                     : [messages.last(where: { $0.role == .user })].compactMap { $0 }
 
-                // Web search via our WebSearchService
-                // Append results to last user message content (matching Python oAI approach)
-                if onlineMode && currentProvider != .openrouter {
-                    if let lastUserIdx = messagesToSend.lastIndex(where: { $0.role == .user }) {
-                        Log.search.info("Running web search for tool-aware path (\(currentProvider.displayName))")
-                        let results = await WebSearchService.shared.search(query: messagesToSend[lastUserIdx].content)
-                        if !results.isEmpty {
-                            let searchContext = "\n\n\(WebSearchService.shared.formatResults(results))\n\nPlease use the above web search results to help answer the user's question."
-                            messagesToSend[lastUserIdx].content += searchContext
-                            Log.search.info("Injected \(results.count) search results into user message")
-                        }
-                    }
-                }
-
                 let systemPrompt: [String: Any] = [
                     "role": "system",
                     "content": systemContent
@@ -1281,7 +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 {
@@ -1297,7 +1275,14 @@ 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
+                if let continuePrompt = silentContinuePrompt {
+                    apiMessages.append(["role": "user", "content": continuePrompt])
+                    silentContinuePrompt = nil
                 }
 
                 let maxIterations = 10  // Increased from 5 to reduce hitting client-side limit
@@ -1311,13 +1296,15 @@ Don't narrate future actions ("Let me...") - just use the tools.
                         break
                     }
 
-                    let response = try await provider.chatWithToolMessages(
-                        model: effectiveModelId,
-                        messages: apiMessages,
-                        tools: tools,
-                        maxTokens: settings.maxTokens > 0 ? settings.maxTokens : nil,
-                        temperature: settings.temperature > 0 ? settings.temperature : nil
-                    )
+                    let response = try await withOverloadedRetry {
+                        try await provider.chatWithToolMessages(
+                            model: effectiveModelId,
+                            messages: apiMessages,
+                            tools: tools,
+                            maxTokens: settings.maxTokens > 0 ? settings.maxTokens : nil,
+                            temperature: settings.temperature > 0 ? settings.temperature : nil
+                        )
+                    }
 
                     if let usage = response.usage { totalUsage = usage }
 
@@ -1336,7 +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
 
@@ -1365,7 +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
@@ -1387,6 +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)")
@@ -1487,7 +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,
@@ -1497,6 +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
@@ -1532,6 +1537,11 @@ Don't narrate future actions ("Let me...") - just use the tools.
             return "Server error. The provider may be experiencing issues. Try again shortly."
         }
 
+        // Overloaded / 529
+        if desc.contains("529") || desc.lowercased().contains("overloaded") {
+            return "API is overloaded. Please try again shortly."
+        }
+
         // Timeout patterns
         if desc.lowercased().contains("timed out") || desc.lowercased().contains("timeout") {
             return "Request timed out. Try a shorter message or different model."
@@ -1541,6 +1551,30 @@ Don't narrate future actions ("Let me...") - just use the tools.
         return desc
     }
 
+    /// Retry an async operation on overloaded (529) errors with exponential backoff.
+    private func withOverloadedRetry<T>(maxAttempts: Int = 4, operation: () async throws -> T) async throws -> T {
+        var attempt = 0
+        while true {
+            do {
+                return try await operation()
+            } catch {
+                let desc = error.localizedDescription
+                let isOverloaded = desc.contains("529") || desc.lowercased().contains("overloaded")
+                attempt += 1
+                if isOverloaded && attempt < maxAttempts && !Task.isCancelled {
+                    let delay = Double(1 << attempt) // 2s, 4s, 8s
+                    Log.api.warning("API overloaded, retrying in \(Int(delay))s (attempt \(attempt)/\(maxAttempts - 1))...")
+                    await MainActor.run {
+                        showSystemMessage("⏳ API overloaded, retrying in \(Int(delay))s… (attempt \(attempt)/\(maxAttempts - 1))")
+                    }
+                    try await Task.sleep(nanoseconds: UInt64(delay * 1_000_000_000))
+                } else {
+                    throw error
+                }
+            }
+        }
+    }
+
     // MARK: - Helpers
 
     private func showModelInfo(_ model: ModelInfo) {

oAI/Views/Main/ChatView.swift

@@ -81,40 +81,6 @@ struct ChatView: View {
                 }
             }
 
-            // Auto-continue countdown banner
-            if viewModel.isAutoContinuing {
-                HStack(spacing: 12) {
-                    ProgressView()
-                        .progressViewStyle(.circular)
-                        .scaleEffect(0.7)
-
-                    VStack(alignment: .leading, spacing: 2) {
-                        Text(ThinkingVerbs.random())
-                            .font(.system(size: 13, weight: .medium))
-                            .foregroundColor(.oaiPrimary)
-                        Text("Continuing in \(viewModel.autoContinueCountdown)s")
-                            .font(.system(size: 11))
-                            .foregroundColor(.oaiSecondary)
-                    }
-
-                    Spacer()
-
-                    Button("Cancel") {
-                        viewModel.cancelAutoContinue()
-                    }
-                    .buttonStyle(.bordered)
-                    .controlSize(.small)
-                    .tint(.red)
-                }
-                .padding(.horizontal, 16)
-                .padding(.vertical, 10)
-                .background(Color.blue.opacity(0.1))
-                .overlay(
-                    Rectangle()
-                        .stroke(Color.blue.opacity(0.3), lineWidth: 1)
-                )
-            }
-
             // Input bar
             InputBar(
                 text: $viewModel.inputText,
@@ -140,6 +106,16 @@ struct ChatView: View {
         .sheet(isPresented: $viewModel.showSkills) {
             AgentSkillsView()
         }
+        .sheet(item: Binding(
+            get: { MCPService.shared.pendingBashCommand },
+            set: { _ in }
+        )) { pending in
+            BashApprovalSheet(
+                pending: pending,
+                onApprove: { forSession in MCPService.shared.approvePendingBashCommand(forSession: forSession) },
+                onDeny: { MCPService.shared.denyPendingBashCommand() }
+            )
+        }
     }
 }
 

oAI/Views/Main/ContentView.swift

@@ -63,8 +63,7 @@ struct ContentView: View {
                 selectedModel: chatViewModel.selectedModel,
                 onSelect: { model in
                     let oldModel = chatViewModel.selectedModel
-                    chatViewModel.selectedModel = model
-                    SettingsService.shared.defaultModel = model.id
+                    chatViewModel.selectModel(model)
                     chatViewModel.showModelSelector = false
                     // Trigger auto-save on model switch
                     Task {

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
@@ -221,7 +221,7 @@ struct SyncStatusFooter: View {
     }
 
     private func updateSyncStatus() {
-        if let error = gitSync.lastSyncError {
+        if gitSync.lastSyncError != nil {
             syncText = "Sync Error"
             syncColor = .red
         } else if gitSync.isSyncing {

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/BashApprovalSheet.swift

@@ -0,0 +1,128 @@
+//
+//  BashApprovalSheet.swift
+//  oAI
+//
+//  Approval UI for AI-requested bash commands
+//
+// 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 SwiftUI
+
+struct BashApprovalSheet: View {
+    let pending: MCPService.PendingBashCommand
+    let onApprove: (_ forSession: Bool) -> Void
+    let onDeny: () -> Void
+
+    var body: some View {
+        VStack(alignment: .leading, spacing: 20) {
+            // Header
+            HStack(spacing: 12) {
+                Image(systemName: "terminal.fill")
+                    .font(.title2)
+                    .foregroundStyle(.orange)
+                VStack(alignment: .leading, spacing: 2) {
+                    Text("Allow Shell Command?")
+                        .font(.system(size: 17, weight: .semibold))
+                    Text("The AI wants to run the following command")
+                        .font(.system(size: 13))
+                        .foregroundStyle(.secondary)
+                }
+                Spacer()
+            }
+
+            // Command display
+            VStack(alignment: .leading, spacing: 6) {
+                Text("COMMAND")
+                    .font(.system(size: 11, weight: .medium))
+                    .foregroundStyle(.secondary)
+                ScrollView {
+                    Text(pending.command)
+                        .font(.system(size: 13, design: .monospaced))
+                        .foregroundStyle(.primary)
+                        .frame(maxWidth: .infinity, alignment: .leading)
+                        .textSelection(.enabled)
+                        .padding(12)
+                }
+                .frame(maxHeight: 180)
+                .background(Color.secondary.opacity(0.08))
+                .clipShape(RoundedRectangle(cornerRadius: 8))
+                .overlay(
+                    RoundedRectangle(cornerRadius: 8)
+                        .stroke(Color.secondary.opacity(0.2), lineWidth: 1)
+                )
+            }
+
+            // Working directory
+            HStack(spacing: 6) {
+                Image(systemName: "folder")
+                    .font(.system(size: 12))
+                    .foregroundStyle(.secondary)
+                Text("Working directory:")
+                    .font(.system(size: 12))
+                    .foregroundStyle(.secondary)
+                Text(pending.workingDirectory)
+                    .font(.system(size: 12, design: .monospaced))
+                    .foregroundStyle(.secondary)
+            }
+
+            // Warning banner
+            HStack(alignment: .top, spacing: 8) {
+                Image(systemName: "exclamationmark.triangle.fill")
+                    .foregroundStyle(.orange)
+                    .font(.system(size: 13))
+                    .padding(.top, 1)
+                Text("Shell commands have full access to your system. Only approve commands you understand and trust.")
+                    .font(.system(size: 12))
+                    .foregroundStyle(.secondary)
+                    .fixedSize(horizontal: false, vertical: true)
+            }
+            .padding(10)
+            .background(Color.orange.opacity(0.08))
+            .clipShape(RoundedRectangle(cornerRadius: 8))
+
+            // Buttons
+            HStack(spacing: 8) {
+                Button("Deny") {
+                    onDeny()
+                }
+                .buttonStyle(.bordered)
+                .tint(.red)
+                .keyboardShortcut(.escape, modifiers: [])
+
+                Spacer()
+
+                Button("Allow Once") {
+                    onApprove(false)
+                }
+                .buttonStyle(.bordered)
+                .tint(.orange)
+
+                Button("Allow for Session") {
+                    onApprove(true)
+                }
+                .buttonStyle(.borderedProminent)
+                .tint(.orange)
+                .keyboardShortcut(.return, modifiers: [])
+            }
+        }
+        .padding(24)
+        .frame(width: 480)
+    }
+}

oAI/Views/Screens/HelpView.swift

@@ -33,6 +33,7 @@ struct CommandDetail: Identifiable {
     let brief: String
     let detail: String
     let examples: [String]
+    var shortcut: String? = nil
 }
 
 struct CommandCategory: Identifiable {
@@ -50,13 +51,15 @@ private let helpCategories: [CommandCategory] = [
             command: "/history",
             brief: "View command history",
             detail: "Opens a searchable modal showing all your previous messages with timestamps in European format (dd.MM.yyyy HH:mm:ss). Search by text content or date to find specific messages. Click any entry to reuse it.",
-            examples: ["/history"]
+            examples: ["/history"],
+            shortcut: "⌘H"
         ),
         CommandDetail(
             command: "/clear",
             brief: "Clear chat history",
             detail: "Removes all messages from the current session and resets the conversation. This does not delete saved conversations.",
-            examples: ["/clear"]
+            examples: ["/clear"],
+            shortcut: "⌘K"
         ),
         CommandDetail(
             command: "/retry",
@@ -82,7 +85,8 @@ private let helpCategories: [CommandCategory] = [
             command: "/model",
             brief: "Select AI model",
             detail: "Opens the model selector to browse and choose from available models. The list depends on your active provider and API key.",
-            examples: ["/model"]
+            examples: ["/model"],
+            shortcut: "⌘M"
         ),
         CommandDetail(
             command: "/provider [name]",
@@ -108,19 +112,22 @@ 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",
             brief: "Load saved conversation",
             detail: "Opens the conversation list to browse and load a previously saved conversation. Replaces the current chat.",
-            examples: ["/load"]
+            examples: ["/load"],
+            shortcut: "⌘L"
         ),
         CommandDetail(
             command: "/list",
             brief: "List saved conversations",
             detail: "Opens the conversation list showing all saved conversations with their dates and message counts.",
-            examples: ["/list"]
+            examples: ["/list"],
+            shortcut: "⌘L"
         ),
         CommandDetail(
             command: "/delete <name>",
@@ -178,13 +185,15 @@ private let helpCategories: [CommandCategory] = [
             command: "/config",
             brief: "Open settings",
             detail: "Opens the settings panel where you can configure providers, API keys, MCP permissions, appearance, and more. Also available via /settings.",
-            examples: ["/config", "/settings"]
+            examples: ["/config", "/settings"],
+            shortcut: "⌘,"
         ),
         CommandDetail(
             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"
         ),
     ]),
 ]
@@ -461,6 +470,15 @@ private struct CommandRow: View {
 
                     Spacer()
 
+                    if let shortcut = command.shortcut {
+                        Text(shortcut)
+                            .font(.system(size: 11, weight: .medium))
+                            .foregroundStyle(.secondary)
+                            .padding(.horizontal, 6)
+                            .padding(.vertical, 2)
+                            .background(.quaternary, in: RoundedRectangle(cornerRadius: 5))
+                    }
+
                     Image(systemName: "chevron.right")
                         .font(.caption)
                         .foregroundStyle(.tertiary)

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) {