MacinAI is an AI chat client that brings modern artificial intelligence to vintage Macintosh systems running System 7.5.3 and later. Chat with ChatGPT (GPT-4o-mini) directly from your classic Mac, with full conversation management, AI-controlled system actions, and an authentic System 7 interface.
Beta 2.1 introduces automatic updates, time synchronization, integrated bug reporting, and a built-in beta guide - making future beta testing seamless and effortless.
Extract to your hard drive (Applications folder recommended)
Double-click MacinAI to launch
First Launch:
MacinAI creates a "MacinAI Settings" file in your System Folder Preferences
Settings are shared across all versions of MacinAI
A "Conversations" folder is created next to the application
Upgrading from Beta 2.0
Your settings file is compatible - no changes needed
Conversations will continue to work
After installing 2.1, all future updates will be automatic!
Upgrading from Beta 1.x
Delete "MacinAI Settings" from your Preferences folder before first launch
Old conversations are backwards compatible and will load correctly
Start fresh with new settings for best results
Getting Started
Step 1: Launch MacinAI
On launch, you'll see the splash screen with MacinAI branding. Click anywhere to continue. MacinAI will:
Test connection to the server
Check for available updates
Check if your clock needs synchronization
Open the main chat interface
Step 2: Enable AI System Control (Optional)
To use AI System Actions (launching apps, opening control panels, etc.):
Click the Settings button (gear icon in toolbar)
Find "AI System Control" section
Click "Enable"
Read and accept the warning dialog
Select "System Info + App List" when prompted
Wait for indexing to complete (10-60 seconds)
After indexing, try asking:
"What apps do I have installed?"
"Open SimpleText"
"Show my TCP/IP settings"
"What's my Mac's memory configuration?"
Step 3: Start Chatting!
Type your message in the input box at the bottom
Press Enter or click Send
Watch the "AI is thinking..." indicator
AI response appears in the conversation area
Save your conversation with CMD+S
Interface Overview
Toolbar (Top)
Left Icon - Toggle sidebar (folder/menu icon)
Center Icon - MacinAI logo
Right Icon - New chat button
Sidebar (Left)
+ New Chat - Start fresh conversation
Conversation List - Click to load saved conversations
Up/Down Arrows - Scroll through list
Auto-Sorting - Most recent always at top
Main Area
Output Area - Scrollable conversation history
Input Box - Multi-line text input with scrollbar
Send Button - Arrow icon to send message
Status Bar (Bottom)
Connection Status - Color-coded dot + status text:
Green - Online (all requests succeeding)
Yellow - Degraded (1 recent failure)
Orange - Failing (2 consecutive failures)
Red - Offline (3+ failures)
Thinking Indicator - "AI is thinking..." with animated dots
Elapsed Time - Shows after 10 seconds: "(15 seconds)"
Keyboard Shortcuts
FILE MENU
CMD+N New conversation window
CMD+O Open conversation file
CMD+S Save conversation
CMD+SHIFT+S Save As (export)
CMD+W Close window
CMD+Q Quit MacinAI
EDIT MENU
CMD+C Copy selected text
CMD+V Paste from clipboard
CMD+X Cut selected text
CMD+A Select all text
MESSAGING
ENTER Send message
SHIFT+ENTER New line in input
NAVIGATION
TAB Move between input/output areas
Arrow Keys Navigate in Beta Guide pages
New Features: How to Use
Automatic Updates
When a new version is available, MacinAI will show an update dialog on launch:
Review the changelog to see what's new
Click "Update Now" to download and install
MacinAI downloads the update and migrates your Conversations folder
The new version launches automatically
You can also click "Remind Later" to defer
Note: After Beta 2.1, you'll never need to manually download updates again!
Time Synchronization
If your Mac's clock differs from server time by more than 90 seconds:
A Time Sync dialog appears
Select your timezone from the dropdown
Review the time difference displayed
Click "Sync" to update your Mac's clock
Verify in the Date & Time control panel
DST Note: After syncing, verify your location in the Date & Time control panel (Map section) for automatic DST adjustments.
Bug Reporting
To submit a bug report:
Click Apple Menu → About MacinAI
Click "Information" button
Click "Bug Report" button
Fill in the three fields:
Description - What happened?
Steps to Reproduce - How to trigger the bug
Expected Behavior - What should happen instead
Optionally check "Attach Debug Logs" and "Attach Conversation"
Click "Submit"
Tip: Enable Debug Mode in Settings before reproducing bugs for more detailed logs!
Beta Guide
To access the built-in beta guide:
Click Apple Menu → About MacinAI
Click "Information" button
Click "Beta Guide" button
Use Prev/Next buttons or arrow keys to navigate
Click page titles in the sidebar for quick navigation
Guide pages include: What's New, Features to Test, Known Issues, Bug Reporting, Examples, and Coming Next.
Debug Mode
To enable debug logging:
Open Settings dialog
Find "Beta Testing" section
Check "Enable Debug Logging"
Optionally check "Verbose Mode" for detailed logs
Click OK
Restart MacinAI for changes to take effect
Debug logs are saved to the Logs folder next to the application.
What to Test
Critical Priority (Test First!)
Auto-Update - When 2.1.1 is released, verify the update process works
Time Sync - Test timezone selection and clock synchronization
Bug Reporting - Submit a test bug report
AI System Actions - Test launching apps, querying system info
Screen Rendering - Verify NO blanking during scroll/type/resize
High Priority
System 7.5.3 Compatibility - Primary target system
Connection Reliability - Server communication
File Save/Load - Conversation management
Memory Leaks - Long-running stability
Beta Guide Navigation - All 6 pages work correctly
Medium Priority
Mac OS 9 Compatibility - Secondary target system
Multiple Windows - CMD+N functionality
Clipboard Integration - Copy/paste across apps
Large Conversations - 100+ message performance
DST Transition - When DST changes occur
Known Limitations
DNS Lookups - May take 5-10 seconds on vintage hardware
No Message Editing - Can't edit sent messages (by design)
No Search - No conversation search yet (planned)
ASCII Text - Best results with standard ASCII
ChatGPT Only - Other AI models planned for future
No Undo - Edit menu Undo is disabled
No Streaming - Responses appear all at once
Full Index Not Implemented - Only "System Info + App List" works for indexing
Time Sync Emulator Issues - May not work correctly in SheepShaver/Basilisk II
Troubleshooting
"Connection Failed" Error
Check server address in Settings (should be ai.oldapplestuff.com)
Verify network connectivity (can you browse the web?)
Confirm TCP/IP control panel has DNS servers configured
Try using IP address instead of hostname
Update Download Fails
Ensure stable network connection
Try again - network timeouts can occur
Check you have enough disk space (~500KB)
Manually download from beta repository if needed
Time Sync Shows Wrong Time
Verify your timezone selection is correct
Check Date & Time control panel Map section
Note: Emulators may not sync correctly - use real hardware
If PRAM battery is dead, sync may not persist
AI Can't Launch Apps
Verify AI System Control is enabled in Settings
Check "Status: Indexed" appears in Settings
Verify you selected "System Info + App List" during indexing
Try asking "What apps do I have?" to verify catalog uploaded
Bug Report Won't Submit
Ensure you have network connectivity
Fill in all three text fields
Try unchecking "Attach Debug Logs" if logs are very large
Use the manual bug reporting method below
How to Report Issues
Preferred Method: Use the built-in Bug Report feature (About → Information → Bug Report)
Alternative Methods:
Post in the MacinAI Beta group chat with details
Email alex@oldapplestuff.com with bug description
Save conversation as "Bug Report - [Description].oas" and share
Good Bug Reports Include:
What you were doing - Step-by-step actions
What happened - Exact error message or behavior
What you expected - What should have happened
Your system - Mac model, System version, memory
Can you reproduce it? - Does it happen every time?
Privacy & Data
What MacinAI Stores Locally:
Conversation files (.oas) in your Conversations folder
Settings file in System Folder Preferences
System catalog (when indexed) - list of apps, volumes, system info
Debug logs (only if enabled)
What Gets Sent to Server:
Messages you send to ChatGPT
Connection test pings
System catalog (when you enable AI System Control)
Bug reports (when you submit them)
Time sync requests
What Does NOT Leave Your Mac:
File contents (unless you explicitly share them)
Personal documents
Passwords or credentials
Settings file (stays local)
Frequently Asked Questions
Q: Which AI model does MacinAI use?
A: Currently ChatGPT (GPT-4o-mini). Other models are planned for future releases.
Q: Will MacinAI update automatically now?
A: Yes! After installing Beta 2.1, all future updates are automatic. MacinAI checks for updates on launch.
Q: Is there a message limit?
A: No message limits during the beta testing period!
Q: Does MacinAI work offline?
A: You can read saved conversations offline (read-only), but can't send new messages.
Q: Can I run multiple conversations at once?
A: Yes! Use CMD+N to open additional windows.
Q: Why does Time Sync prompt me on launch?
A: MacinAI checks if your clock differs from server time by more than 90 seconds. This ensures accurate timestamps.
Q: Is AI System Control safe?
A: Yes. AI can only perform actions you could do yourself. Power management (shutdown/restart) requires confirmation dialogs.
Q: Can I disable AI System Control later?
A: Yes. Go to Settings and click "Disable". Your system catalog will be deleted from the server.
Q: What's the .oas file format?
A: "Old Apple Stuff" - plain text files with metadata header. Open with any text editor.
Q: Why is connection testing slow?
A: DNS lookups on vintage Mac OS are synchronous and can take 5-10 seconds. This is normal.
Coming Next
Features planned for future beta releases:
Additional AI Models - Claude, Gemini, Grok support
Streaming Responses - Character-by-character AI responses
Advanced System Actions - Read/write files, find files by content
Conversation Search - Search within and across conversations
Export to Text - Export conversations as plain text
Your testing helps make MacinAI better for the entire vintage Mac community. With Beta 2.1's automatic updates and integrated bug reporting, providing feedback is easier than ever.
Every bug report, suggestion, and piece of feedback contributes to creating the best possible AI chat experience for classic Macintosh systems.
Happy testing!
- Alex Hoopes
alex@oldapplestuff.com
Quick Reference Card
NEW IN BETA 2.1
================
- Automatic Updates (one-click)
- Time Synchronization (27 timezones, DST support)
- Integrated Bug Reporting
- Beta Guide Window (6 pages)
- Debug Mode Toggle
- System Power Call Handling
- About Dialog Info Button
KEYBOARD SHORTCUTS
===================
CMD+N New conversation
CMD+S Save conversation
CMD+SHIFT+S Save As
CMD+O Open file
CMD+W Close window
CMD+Q Quit
CMD+C Copy
CMD+V Paste
CMD+X Cut
CMD+A Select All
ENTER Send message
SHIFT+ENTER New line
AI SYSTEM COMMANDS
===================
"Open SimpleText" Launch application
"Show TCP/IP settings" Open control panel
"What apps do I have?" Query system
"Restart my Mac" Power management
"What's my RAM?" System information
STATUS BAR COLORS
==================
Green = Online (all OK)
Yellow = Degraded (1 failure)
Orange = Failing (2 failures)
Red = Offline (3+ failures)
ACCESSING NEW FEATURES
======================
Bug Report: About → Information → Bug Report
Beta Guide: About → Information → Beta Guide
Debug Mode: Settings → Beta Testing section
Time Sync: Automatic on launch (if needed)
Updates: Automatic on launch (if available)
MacinAI Beta 2.1.0 Released: December 1, 2025 AI Model: ChatGPT (GPT-4o-mini) Icon Design: Janez J. Starc