oai-swift/README.md

oAI

A powerful native macOS AI chat application with support for multiple providers, advanced memory management, and seamless Git synchronization.

Features

🤖 Multi-Provider Support

• OpenAI - GPT models with native API support
• Anthropic - Claude models with OAuth integration
• OpenRouter - Access to 300+ AI models from multiple providers
• Ollama - Local model inference for privacy

💬 Core Chat Capabilities

• Streaming Responses - Real-time token streaming for faster interactions
• Conversation Management - Save, load, export, and search conversations
• File Attachments - Support for text files, images, and PDFs
• Image Generation - Create images with supported models (DALL-E, Flux, etc.)
• Online Mode - DuckDuckGo and Google web search integration
• Session Statistics - Track token usage, costs, and response times
• Command History - Navigate previous commands with searchable modal (⌘H)

🧠 Enhanced Memory & Context System

• Smart Context Selection - Automatically select relevant messages to reduce token usage by 50-80%
• Message Starring - Mark important messages to always include them in context
• Semantic Search - AI-powered search across conversations using embeddings
• Progressive Summarization - Automatically summarize old portions of long conversations
• Multi-Provider Embeddings - Support for OpenAI, OpenRouter, and Google embeddings

🔧 Model Context Protocol (MCP)

Advanced filesystem access for AI models with fine-grained permissions:

• Read Access - Allow AI to read files in specified folders
• Write Access - Optional write permissions for file modifications
• Gitignore Support - Respects .gitignore patterns when listing/searching
• Folder Management - Add/remove allowed folders with visual status
• Search Operations - Find files by name or content across allowed directories

🔄 Git Synchronization

Seamless conversation backup and sync across devices:

• Auto-Sync - Automatic export and push to Git repository
• Smart Triggers - Sync on app start, idle, goodbye phrases, model switches, or app quit
• Multi-Provider Support - GitHub, GitLab, Gitea, and custom Git servers
• Conflict Prevention - Warning system for multi-machine usage
• Manual Sync - One-click sync with progress indication

📧 Email Handler (AI Email Assistant)

Automated email responses powered by AI:

• IMAP Polling - Monitor inbox for emails with specific subject identifiers
• AI-Powered Responses - Generate contextual replies using any AI provider
• SMTP Integration - Send replies via SMTP with TLS support
• Rate Limiting - Configurable emails per hour limit
• Email Threading - Proper In-Reply-To headers for email chains
• Secure Storage - AES-256-GCM encryption for all credentials
• Email Log - Track all processed emails with success/error status

🎨 UI/UX

• Native macOS interface with dark/light mode support
• Markdown rendering with syntax highlighting
• Customizable text sizes (GUI, dialog, input)
• Footer stats display (messages, tokens, cost, sync status)
• Header status indicators (MCP, Online mode, Git sync)
• Responsive message layout with copy buttons

Installation

Download

Download the latest release from the Releases page. Two builds are available:

• oAI-x.x.x-AppleSilicon.dmg — for Macs with an Apple Silicon chip (M1 and later)
• oAI-x.x.x-Universal.dmg — runs natively on both Apple Silicon and Intel Macs

Installing from DMG

1. Open the downloaded .dmg file
2. Drag oAI.app into the Applications folder
3. Eject the DMG
4. Launch oAI from Applications or Spotlight

First Launch — Gatekeeper Warning

oAI is signed by the developer but has not yet been notarized by Apple. Notarization is Apple's automated malware scan — the app itself is safe, but macOS Gatekeeper may block it on first launch with a message saying the app "cannot be opened because the developer cannot be verified."

To open the app, you have two options:

Option A — Right-click to open (quickest):

1. Right-click (or Control-click) oAI.app in Applications
2. Select Open from the context menu
3. Click Open in the dialog that appears
4. After doing this once, the app opens normally from then on

Option B — Remove the quarantine flag via Terminal:

xattr -dr com.apple.quarantine /Applications/oAI.app

This command removes the quarantine attribute that macOS attaches to files downloaded from the internet. The -d flag deletes the attribute, -r applies it recursively to the app bundle. Once removed, macOS no longer blocks the app from launching.

Requirements

• macOS 14.0 (Sonoma) or later
• An API key for at least one supported provider (OpenRouter, Anthropic, OpenAI, or Google), or Ollama running locally

Configuration

API Keys

Add your API keys in Settings (⌘,) → General tab:

• OpenAI - Get from OpenAI Platform
• Anthropic - Get from Anthropic Console or use OAuth
• OpenRouter - Get from OpenRouter Keys
• Ollama - Base URL (default: http://localhost:11434)
• Google - API key used for Google Custom Search (web search) and Google embeddings (semantic search) — not a chat provider

Essential Settings

General Tab

• Default Provider - Select your preferred AI provider
• Streaming - Enable/disable real-time response streaming
• Memory - Control conversation context (on/off)
• Online Mode - Enable web search integration
• Max Tokens - Set maximum response length
• Temperature - Control response randomness (0.0 - 2.0)

Advanced Tab

• Smart Context Selection - Reduce token usage automatically
• Semantic Search - Enable AI-powered conversation search
• Progressive Summarization - Handle long conversations efficiently

Sync Tab

• Repository URL - Git repository for conversation backup
• Authentication - Username/password or access token
• Auto-Save - Configure automatic save triggers
• Manual Sync - One-click synchronization

Email Tab

• Email Handler - Configure automated email responses
• IMAP/SMTP Settings - Email server configuration
• AI Provider - Select which AI to use for responses
• Rate Limiting - Control email processing frequency

Slash Commands

Model & Chat

• /help - Show help and available commands
• /model - Open model selector (⌘M)
• /clear - Clear current conversation
• /retry - Regenerate last response
• /info [model] - Display model information

Conversation Management

• /save <name> - Save current conversation
• /load or /list - List and load saved conversations (⌘L)
• /delete <name> - Delete a saved conversation
• /export <md|json> [filename] - Export conversation
• /history - Open command history modal (⌘H)

Provider & Settings

• /provider [name] - Switch or display current provider
• /config or /settings - Open settings (⌘,)
• /stats - View session statistics
• /credits - Check API credits/balance (OpenRouter)

Features

• /memory <on|off> - Toggle conversation memory
• /online <on|off> - Toggle online/web search mode
• /mcp <on|off|status|add|remove|list|write> - Manage MCP filesystem access

MCP (Model Context Protocol)

• /mcp add <path> - Grant AI access to a folder
• /mcp remove <index|path> - Revoke folder access
• /mcp list - Show allowed folders
• /mcp write <on|off> - Enable/disable file write permissions
• /mcp status - Display MCP configuration

File Attachments

Attach files to your messages using the syntax: @/path/to/file

Example:

Can you review this code? @~/project/main.swift

Supported formats:

• Text files - Any UTF-8 text file (.txt, .md, .swift, .py, .json, etc.)
• Images - PNG, JPG, WebP (for vision-capable models)
• PDFs - Document analysis with vision models

Limits:

• Maximum file size: 10 MB
• Text files truncated after 50 KB (head + tail shown)
• Image dimensions automatically scaled for optimal processing

Keyboard Shortcuts

• ⌘M - Open model selector
• ⌘, - Open settings
• ⌘N - New conversation
• ⌘L - List saved conversations
• ⌘H - Command history
• Esc - Cancel generation / Close dropdown
• ↑/↓ - Navigate command dropdown (when typing /)
• Return - Send message
• Shift+Return - Insert newline

Advanced Features

Smart Context Selection

Reduce token usage by 50-80% without losing context quality:

• Always includes last 10 messages
• Prioritizes user-starred messages
• Includes high-importance messages (based on cost and length)
• Respects model context limits automatically

Semantic Search

Find conversations by meaning, not just keywords:

• AI-powered embeddings using OpenAI, OpenRouter, or Google
• Search across all conversations semantically
• Cost-effective: ~$0.04 one-time for 10k messages
• Toggle semantic search in conversation list

Progressive Summarization

Handle 100+ message conversations gracefully:

• Automatically summarizes old portions of conversations
• Keeps last 20 messages in full
• Summaries included in context for continuity
• Configurable threshold (default: 50 messages)

Git Synchronization

Backup and sync conversations across devices:

• Export Format: Markdown files for human readability
• Auto-Sync Options:
  • On app start (pull + import only)
  • On idle (configurable timeout)
  • After goodbye phrases ("bye", "thanks", "goodbye")
  • On model switch
  • On app quit
  • Minimum message count threshold
• Manual Sync: One-click full sync (export + pull + push)

Email Handler

AI-powered email auto-responder:

• Monitoring: IMAP polling every 30 seconds
• Filtering: Subject identifier (e.g., [JARVIS])
• Processing: AI generates contextual responses
• Sending: SMTP with TLS (port 465 recommended)
• Tracking: Email log with success/error status
• Security: AES-256-GCM encrypted credentials

Development

Project Structure

oAI/
├── Models/              # Data models
│   ├── Message.swift           # Chat message model
│   ├── Conversation.swift      # Saved conversation model
│   ├── ModelInfo.swift         # AI model metadata
│   └── Settings.swift          # App settings enums
│
├── Views/               # SwiftUI views
│   ├── Main/                   # Primary UI components
│   │   ├── ChatView.swift      # Main chat interface
│   │   ├── MessageRow.swift    # Individual message display
│   │   ├── InputBar.swift      # Message input with commands
│   │   ├── HeaderView.swift    # Top bar (provider/model/status)
│   │   └── FooterView.swift    # Bottom stats bar
│   │
│   └── Screens/                # Modal/sheet views
│       ├── SettingsView.swift  # Settings with tabs
│       ├── ModelSelectorView.swift
│       ├── ConversationListView.swift
│       └── HelpView.swift
│
├── ViewModels/          # Observable view models
│   └── ChatViewModel.swift     # Main chat logic & state
│
├── Providers/           # AI provider implementations
│   ├── Provider.swift          # Protocol definition
│   ├── OpenRouterProvider.swift
│   ├── AnthropicProvider.swift
│   ├── OpenAIProvider.swift
│   └── OllamaProvider.swift
│
├── Services/            # Business logic & data
│   ├── DatabaseService.swift   # SQLite operations (GRDB)
│   ├── SettingsService.swift   # Settings persistence
│   ├── ProviderRegistry.swift  # AI provider management
│   ├── MCPService.swift        # File access (MCP)
│   ├── WebSearchService.swift  # DuckDuckGo/Google search
│   ├── GitSyncService.swift    # Git synchronization
│   ├── ContextSelectionService.swift  # Smart context
│   ├── EmbeddingService.swift  # Semantic search
│   ├── EmailService.swift      # Email monitoring (IMAP)
│   └── EmailHandlerService.swift  # Email AI responder
│
└── Resources/
    └── oAI.help/               # macOS Help Book

Key Technologies

• SwiftUI - Modern declarative UI framework
• GRDB - SQLite database wrapper for persistence
• MarkdownUI - Markdown rendering with syntax highlighting
• os.Logger - Native logging framework
• Network Framework - Pure Swift IMAP/SMTP implementation
• Security Framework - Keychain and encryption services

Database Schema

Conversations: id, name, createdAt, updatedAt Messages: id, conversationId, role, content, tokens, cost, timestamp Message Metadata: message_id, importance_score, user_starred, summary Message Embeddings: message_id, embedding (BLOB), model, dimension Conversation Summaries: id, conversationId, startIndex, endIndex, summary Email Logs: id, sender, subject, status, timestamp

Building & Debugging

Build Commands:

# Clean build
xcodebuild clean -scheme oAI

# Build
xcodebuild -scheme oAI -configuration Debug

# Run tests
xcodebuild test -scheme oAI

Logs Location:

~/Library/Logs/oAI.log

Database Location:

~/Library/Application Support/oAI/oai_conversations.db

Troubleshooting

Common Issues

API Connection Errors:

• Verify API keys in Settings → General
• Check internet connection
• Ensure provider is not experiencing outages

MCP Not Working:

• Verify folder permissions in Settings → MCP
• Check allowed folders list
• Ensure files are not in .gitignore (if enabled)

Git Sync Errors:

• Verify repository URL and credentials
• Check if repository is initialized (clone first)
• Ensure proper network access to Git server
• Use access token instead of password for GitHub

Email Handler Issues:

• Verify IMAP/SMTP settings and credentials
• Use port 465 for SMTP (direct TLS recommended)
• Check subject identifier matches exactly (case-sensitive)
• Review email logs in Settings → Email → View Email Log

Embedding Errors:

• Configure API key for OpenAI, OpenRouter, or Google
• Check Settings → Advanced → Semantic Search
• Verify embedding provider is selected

Performance Notes

• Context Selection: 50-80% token reduction for long conversations
• Semantic Search: ~$0.02-0.15/month for heavy users
• Conversation Export: Markdown format for human readability
• Database: Indexed queries for fast conversation retrieval
• Streaming: Efficient memory usage with AsyncThrowingStream

Roadmap

• Vector index for faster semantic search (sqlite-vss)
• Local embeddings (sentence-transformers, $0 cost)
• Conversation clustering and recommendations
• Multi-modal conversation export (PDF, HTML)
• Plugin system for custom tools
• iOS companion app with CloudKit sync

License

oAI is free software licensed under the GNU Affero General Public License v3.0 (AGPL-3.0).

This means you are free to use, study, modify, and distribute oAI, but any modified version you run as a network service must also be made available as free software under the same license.

See LICENSE for the full license text, or visit gnu.org/licenses/agpl-3.0.

Author

Rune Olsen

• Website: https://blog.rune.pm
• Gitlab.pm: @rune

Contributing

Contributions are welcome! By submitting a pull request you agree that your contribution will be licensed under the AGPL-3.0.

1. Fork the repository
2. Create a feature branch (git checkout -b feature/amazing-feature)
3. Commit your changes (git commit -m 'Add amazing feature')
4. Push to the branch (git push origin feature/amazing-feature)
5. Open a Pull Request

Please ensure:

• Code follows Swift style guidelines
• All tests pass
• Documentation is updated
• Commit messages are descriptive

Acknowledgments

• MarkdownUI - Excellent markdown rendering library
• GRDB - Robust SQLite wrapper for Swift
• Anthropic, OpenAI, OpenRouter - AI API providers

---

⭐ Star this project if you find it useful!

🐛 Found a bug? Open an issue