macOS Deployment Guide

This guide covers deploying the headroom proxy server as a background service on macOS using LaunchAgent. The service will start automatically on login and restart on crash.

Overview

macOS LaunchAgent provides a native way to run background services with:

• Automatic startup on user login
• Crash recovery with automatic restart
• Standard logging to ~/Library/Logs/
• Native lifecycle management via launchctl

This is ideal for local development environments where you want "set and forget" proxy configuration.

Prerequisites

• macOS 10.13+ (High Sierra or later)
• headroom-ai installed with proxy support
• Anthropic API key configured

Installing Headroom with Proxy Support

# Install with proxy support
pip install headroom-ai[proxy]

# Verify installation
headroom proxy --help

API Key Configuration

Your Anthropic API key can be configured in several ways:

Option 1: Shell environment (recommended)

# Add to ~/.bashrc or ~/.zshrc
export ANTHROPIC_API_KEY="sk-ant-..."

Option 2: LaunchAgent plist

<key>EnvironmentVariables</key>
<dict>
    <key>ANTHROPIC_API_KEY</key>
    <string>sk-ant-...</string>
</dict>

Option 3: System environment

# Add to /etc/launchd.conf (requires admin)
setenv ANTHROPIC_API_KEY sk-ant-...

Quick Install

The automated installer handles all setup:

# Clone or navigate to headroom repository
cd examples/deployment/macos-launchagent

# Run installer
./install.sh

The installer will:

1. Detect your headroom installation
2. Prompt for port configuration (default: 8787)
3. Create log directory
4. Generate LaunchAgent plist
5. Load and start the service
6. Verify service is running

Installation Options

Custom port:

./install.sh --port 9000

Unattended install (no prompts):

./install.sh --port 8787 --unattended

Reinstall over existing:

# Installer will prompt to reinstall if service exists
./install.sh

Manual Installation

If you prefer full control over the installation:

Step 1: Create Log Directory

mkdir -p ~/Library/Logs/headroom

Step 2: Generate LaunchAgent Plist

Copy and customize the template:

cd examples/deployment/macos-launchagent
cp com.headroom.proxy.plist.template ~/Library/LaunchAgents/com.headroom.proxy.plist

Edit ~/Library/LaunchAgents/com.headroom.proxy.plist:

1. Replace __HEADROOM_PATH__ with your headroom path:

command -v headroom
# Example output: /usr/local/bin/headroom

1. Replace __PORT__ with your desired port (e.g., 8787)

2. Replace __HOME__ with your home directory:

echo $HOME
# Example output: /Users/yourusername

Step 3: Load the LaunchAgent

launchctl bootstrap gui/$(id -u) ~/Library/LaunchAgents/com.headroom.proxy.plist

Step 4: Verify Service

# Check if service is running
launchctl print gui/$(id -u)/com.headroom.proxy

# Check if port is listening
lsof -iTCP:8787 -sTCP:LISTEN

# Test health endpoint
curl http://localhost:8787/health

Configuration

Port Customization

The default port is 8787. To use a custom port:

During installation:

./install.sh --port 9000

After installation:

1. Uninstall: ./uninstall.sh
2. Reinstall with new port: ./install.sh --port 9000
3. Update shell integration: export HEADROOM_PROXY_PORT=9000

Log Location

Logs are written to standard macOS locations:

• Standard output: ~/Library/Logs/headroom/proxy.log
• Error output: ~/Library/Logs/headroom/proxy-error.log

To change log locations, edit the plist:

<key>StandardOutPath</key>
<string>/custom/path/proxy.log</string>

Environment Variables

Configure additional options in the plist EnvironmentVariables section:

<key>EnvironmentVariables</key>
<dict>
    <!-- Required: Proxy port -->
    <key>HEADROOM_PROXY_PORT</key>
    <string>8787</string>

    <!-- Optional: API key (or set in shell) -->
    <key>ANTHROPIC_API_KEY</key>
    <string>sk-ant-...</string>

    <!-- Optional: Enable LLMLingua compression -->
    <key>HEADROOM_COMPRESSION_PROVIDER</key>
    <string>llmlingua</string>

    <!-- Optional: LLMLingua device (auto, cuda, cpu, mps) -->
    <key>HEADROOM_LLMLINGUA_DEVICE</key>
    <string>mps</string>
</dict>

Note: LLMLingua requires additional installation:

pip install headroom-ai[llmlingua]

Crash Recovery

The LaunchAgent is configured with:

• KeepAlive: Automatically restarts on crash
• ThrottleInterval: 10 seconds between restart attempts

To disable automatic restart, edit the plist:

<key>KeepAlive</key>
<false/>

Shell Integration

Automatically configure your shell to use the proxy when available.

Setup

Add to ~/.bashrc (bash) or ~/.zshrc (zsh):

# Configure port (optional, defaults to 8787)
export HEADROOM_PROXY_PORT=8787

# Source shell integration
source /path/to/headroom/examples/deployment/macos-launchagent/shell-integration.sh

What It Does

The shell integration script:

1. Checks if proxy is running on configured port
2. If running, sets ANTHROPIC_BASE_URL=http://localhost:8787
3. If not running, attempts to start the LaunchAgent
4. Provides status messages on first load

This makes Claude clients automatically use the proxy without manual configuration.

Manual Configuration

If you prefer not to use shell integration:

# Add to ~/.bashrc or ~/.zshrc
export ANTHROPIC_BASE_URL=http://localhost:8787

Service Management

Check Status

# View service status
launchctl print gui/$(id -u)/com.headroom.proxy

# Check if port is listening
lsof -iTCP:8787 -sTCP:LISTEN

# Test health endpoint
curl http://localhost:8787/health

View Logs

# Tail standard output
tail -f ~/Library/Logs/headroom/proxy.log

# Tail error output
tail -f ~/Library/Logs/headroom/proxy-error.log

# View last 50 lines
tail -n 50 ~/Library/Logs/headroom/proxy-error.log

Restart Service

# Graceful restart (stop and let KeepAlive restart it)
launchctl kickstart -k gui/$(id -u)/com.headroom.proxy

# Manual stop/start
launchctl bootout gui/$(id -u)/com.headroom.proxy
launchctl bootstrap gui/$(id -u) ~/Library/LaunchAgents/com.headroom.proxy.plist

Stop Service Temporarily

# Disable without uninstalling
launchctl disable gui/$(id -u)/com.headroom.proxy

# Re-enable
launchctl enable gui/$(id -u)/com.headroom.proxy

Verification

After installation, verify everything is working:

1. Check Service Status

launchctl print gui/$(id -u)/com.headroom.proxy

Expected output includes:

state = running

2. Check Port

lsof -iTCP:8787 -sTCP:LISTEN

Should show headroom listening on port 8787.

3. Test Health Endpoint

curl http://localhost:8787/health

Expected response:

{"status": "healthy"}

4. Test Proxy Functionality

# Set base URL
export ANTHROPIC_BASE_URL=http://localhost:8787

# Test with Python
python -c "
import anthropic
client = anthropic.Anthropic()
response = client.messages.create(
    model='claude-3-5-sonnet-20241022',
    max_tokens=50,
    messages=[{'role': 'user', 'content': 'Hi'}]
)
print(response.content[0].text)
"

5. Check Logs for Errors

tail -n 20 ~/Library/Logs/headroom/proxy-error.log

Should show no errors. Common startup errors are listed in Troubleshooting.

Troubleshooting

Service Won't Start

Symptom: launchctl print shows service not loaded or failed state

Check logs:

tail -n 50 ~/Library/Logs/headroom/proxy-error.log

Common causes:

Error	Solution
ANTHROPIC_API_KEY not set	Set API key in environment or plist
ModuleNotFoundError: No module named 'headroom'	Install: pip install headroom-ai[proxy]
command not found: headroom	Update plist with correct path: command -v headroom
Address already in use	Change port or stop conflicting service

Port Already in Use

Symptom: Service starts but port not listening, logs show "Address already in use"

Find what's using the port:

lsof -iTCP:8787 -sTCP:LISTEN

Solutions:

1. Stop conflicting service
2. Use different port: ./uninstall.sh && ./install.sh --port 9000

Service Crashes Immediately

Symptom: Service starts but immediately exits

Check for Python errors:

tail -f ~/Library/Logs/headroom/proxy-error.log

Common causes:

• Missing dependencies: pip install headroom-ai[proxy]
• Invalid API key: Verify ANTHROPIC_API_KEY
• Python version incompatible: Requires Python 3.9+

ANTHROPIC_BASE_URL Not Set

Symptom: Shell integration not setting environment variable

Verify proxy is running:

curl http://localhost:8787/health

Reload shell configuration:

source ~/.bashrc  # or ~/.zshrc

Check shell integration is sourced:

# Should be set to 1
echo $HEADROOM_SHELL_INTEGRATION_LOADED

Service Not Auto-Starting on Login

Symptom: Service doesn't start after reboot

Verify LaunchAgent is loaded:

launchctl list | grep headroom

If not listed:

launchctl bootstrap gui/$(id -u) ~/Library/LaunchAgents/com.headroom.proxy.plist

Check RunAtLoad is enabled:

grep -A1 RunAtLoad ~/Library/LaunchAgents/com.headroom.proxy.plist

Should show:

<key>RunAtLoad</key>
<true/>

Permission Issues

Symptom: "Operation not permitted" errors

Ensure plist has correct permissions:

chmod 644 ~/Library/LaunchAgents/com.headroom.proxy.plist

Verify ownership:

ls -l ~/Library/LaunchAgents/com.headroom.proxy.plist

Should be owned by your user, not root.

Uninstallation

Quick Uninstall

cd examples/deployment/macos-launchagent
./uninstall.sh

This will:

1. Stop the service
2. Remove LaunchAgent plist
3. Optionally remove log directory (prompts)

Remove Everything

# Uninstall service and remove logs
./uninstall.sh --remove-logs

# Remove shell integration from ~/.bashrc or ~/.zshrc
# Delete or comment out:
#   export HEADROOM_PROXY_PORT=8787
#   source .../shell-integration.sh

Manual Uninstall

# Stop service
launchctl bootout gui/$(id -u)/com.headroom.proxy

# Remove plist
rm ~/Library/LaunchAgents/com.headroom.proxy.plist

# Remove logs (optional)
rm -rf ~/Library/Logs/headroom

Production Deployment

For production environments, consider:

• System-wide LaunchDaemon instead of per-user LaunchAgent
• Resource limits in plist (CPU, memory)
• Log rotation for long-running deployments
• Monitoring via external tools
• Multiple instances on different ports for redundancy

LaunchAgent is designed for single-user development. For production, evaluate:

• Docker deployment for containerized environments
• systemd on Linux servers
• Cloud-native solutions (ECS, Cloud Run, etc.)

Related Documentation

• Proxy Server Documentation - Core proxy configuration and features
• Configuration Guide - Detailed configuration options
• Architecture - How Headroom works internally
• Troubleshooting - General troubleshooting guide

Platform Alternatives

• Linux: Use systemd instead of LaunchAgent
• Windows: Use Task Scheduler or NSSM (Non-Sucking Service Manager)
• Docker: See proxy.md for containerized deployment

Security Considerations

LaunchAgent vs LaunchDaemon

LaunchAgent (used here):

• Runs in user context
• No root privileges required
• Starts on user login
• Per-user isolation

LaunchDaemon (not covered):

• Runs as root or specific user
• System-wide service
• Starts on boot
• Requires admin privileges

For single-user development, LaunchAgent is recommended for security.

API Key Security

Store API keys securely:

• ✅ Use environment variables in shell config
• ✅ Use macOS Keychain (advanced)
• ✅ Restrict plist file permissions: chmod 600
• ❌ Don't commit API keys to version control
• ❌ Don't store in world-readable files

Network Security

The proxy binds to 127.0.0.1 (localhost only) by default:

• ✅ Only accessible from local machine
• ✅ No external network exposure
• ❌ Don't bind to 0.0.0.0 without firewall rules

Advanced Configuration

Multiple Proxy Instances

Run multiple proxies on different ports:

# Install first instance
./install.sh --port 8787

# For second instance, manually create plist with different label
cp com.headroom.proxy.plist.template ~/Library/LaunchAgents/com.headroom.proxy-2.plist
# Edit: Change Label to com.headroom.proxy-2, port to 8788
launchctl bootstrap gui/$(id -u) ~/Library/LaunchAgents/com.headroom.proxy-2.plist

Custom LaunchAgent Schedule

Run proxy only during business hours:

<!-- Add to plist -->
<key>StartCalendarInterval</key>
<dict>
    <key>Hour</key>
    <integer>9</integer>
    <key>Minute</key>
    <integer>0</integer>
</dict>

Resource Limits

Limit CPU and memory usage:

<!-- Add to plist -->
<key>HardResourceLimits</key>
<dict>
    <key>NumberOfProcesses</key>
    <integer>1</integer>
    <key>MemoryMax</key>
    <integer>536870912</integer> <!-- 512 MB -->
</dict>

FAQ

Q: Why LaunchAgent instead of running headroom proxy manually?

A: LaunchAgent provides automatic startup, crash recovery, and proper lifecycle management. You don't have to remember to start the proxy or keep a terminal window open.

Q: Can I use this in production?

A: LaunchAgent is designed for development. For production, use Docker, systemd, or cloud-native deployment.

Q: How much does the proxy impact performance?

A: Minimal. The proxy adds ~10-50ms latency while reducing token costs by 50-90%. The cost savings far outweigh the latency.

Q: Do I need to restart the proxy when configuration changes?

A: Yes. After changing the plist, reload the service:

launchctl kickstart -k gui/$(id -u)/com.headroom.proxy

Q: Can I use this with multiple API providers?

A: The LaunchAgent setup is Anthropic-specific. For other providers, see proxy.md for configuration options.

Q: Does this work with Apple Silicon (M1/M2/M3)?

A: Yes, fully compatible. For LLMLingua compression, use --llmlingua-device mps for Apple Silicon acceleration.