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Matthew Valancyclaude
Matthew Valancy
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feat: Integrate Tailscale health monitoring into setup
Adds automatic Tailscale health monitoring to GraphDone Core development and production environments. Changes: - scripts/setup-tailscale-monitor.sh - Standalone installer (96 lines) - Creates health check script with 5-second timeout detection - Installs systemd service and timer for 5-minute checks - Auto-restarts tailscaled when frozen/unresponsive - Logs all events to /var/log/tailscale-health.log - tools/setup.sh - Auto-detection and installation - Detects if Tailscale is installed during environment setup - Automatically runs monitoring setup if Tailscale present - Gracefully skips if Tailscale not installed - Provides manual setup instructions if sudo unavailable - docs/infrastructure/tailscale-monitoring.md - Complete documentation - Installation (automatic and manual) - Verification and troubleshooting - Configuration options - Integration with GraphDone architecture This prevents the "zombie Tailscale" issue where daemon runs but hangs, blocking connectivity. Critical for demo instances, multi-server deployments, and developer experience. Related: GraphDone-Devops/monitoring/tailscale Co-Authored-By: Claude <noreply@anthropic.com>
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‎docs/infrastructure/tailscale-monitoring.md‎

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# Tailscale Health Monitoring
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## Overview
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GraphDone Core includes automatic Tailscale health monitoring to ensure reliable mesh networking across all instances.
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## Problem
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Tailscale can enter a "zombie" state where:
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- The daemon process runs but doesn't respond
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- Commands like `tailscale status` hang indefinitely
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- DNS resolution fails (hostnames become unreachable)
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- Network connectivity is lost across the mesh
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This requires manual intervention to restart the service.
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## Solution
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Automated health monitoring that:
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- ✅ Checks Tailscale every 5 minutes
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- ✅ Detects hangs using timeout (not just process checks)
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- ✅ Auto-restarts when unresponsive
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- ✅ Logs all events for debugging
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- ✅ Requires zero manual intervention
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## Installation
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### Automatic (Recommended)
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The monitoring is automatically set up when you run:
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```bash
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./tools/setup.sh
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```
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If Tailscale is installed, the script will detect it and offer to set up monitoring.
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### Manual Installation
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If you need to install it manually:
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```bash
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sudo bash ./scripts/setup-tailscale-monitor.sh
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```
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## Verification
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Check if monitoring is running:
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```bash
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sudo systemctl status tailscale-health-monitor.timer
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```
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View monitoring logs:
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```bash
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sudo cat /var/log/tailscale-health.log
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```
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Check next scheduled run:
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```bash
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systemctl list-timers tailscale-health-monitor.timer
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```
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## How It Works
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### Health Check Logic
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Every 5 minutes, the monitor:
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1. Runs `timeout 5s tailscale status`
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2. If successful → Logs "healthy" and exits
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3. If timeout → Restarts `tailscaled` service
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4. Verifies restart was successful
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5. Logs all actions with timestamps
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### Files Installed
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```
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/usr/local/bin/tailscale-health-monitor.sh # Health check script
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/etc/systemd/system/tailscale-health-monitor.service # Systemd service
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/etc/systemd/system/tailscale-health-monitor.timer # 5-minute timer
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/var/log/tailscale-health.log # Event log
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```
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### Systemd Timer Configuration
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```ini
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[Timer]
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OnBootSec=2min # First check 2 minutes after boot
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OnUnitActiveSec=5min # Then every 5 minutes
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AccuracySec=1s # Precise timing
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```
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## Log Examples
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### Healthy Status
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```
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[2025-11-16 06:15:00] Starting Tailscale health check (GraphDone Core)...
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[2025-11-16 06:15:01] ✓ Tailscale is healthy
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```
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### Auto-Recovery
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```
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[2025-11-16 06:20:00] Starting Tailscale health check (GraphDone Core)...
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[2025-11-16 06:20:05] ✗ Tailscale is frozen or unresponsive
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[2025-11-16 06:20:05] Restarting tailscaled service...
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[2025-11-16 06:20:08] ✓ Tailscale successfully restarted
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```
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## Troubleshooting
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### Timer not running
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Enable and start the timer:
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```bash
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sudo systemctl enable tailscale-health-monitor.timer
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sudo systemctl start tailscale-health-monitor.timer
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```
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### Check for errors
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View systemd journal:
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```bash
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sudo journalctl -u tailscale-health-monitor.service -n 50
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```
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### Manually trigger check
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```bash
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sudo systemctl start tailscale-health-monitor.service
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```
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### Disable monitoring
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```bash
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sudo systemctl stop tailscale-health-monitor.timer
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sudo systemctl disable tailscale-health-monitor.timer
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```
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## Integration with GraphDone
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This monitoring is critical for GraphDone Core because:
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1. **Demo Instances**: Demo servers need reliable mesh connectivity
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2. **Multi-Server Deployments**: Clusters rely on Tailscale for service discovery
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3. **Developer Experience**: Frozen Tailscale blocks local development
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4. **Production Reliability**: Auto-recovery prevents manual intervention
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## Configuration
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### Modify Check Interval
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Edit the timer file:
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```bash
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sudo nano /etc/systemd/system/tailscale-health-monitor.timer
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```
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Change `OnUnitActiveSec=5min` to desired interval, then:
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```bash
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sudo systemctl daemon-reload
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sudo systemctl restart tailscale-health-monitor.timer
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```
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### Modify Timeout
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Edit the health check script:
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```bash
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sudo nano /usr/local/bin/tailscale-health-monitor.sh
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```
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Change `TIMEOUT=5` to desired value (in seconds).
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## Related Documentation
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- [GraphDone DevOps Monitoring](../../../GraphDone-Devops/monitoring/tailscale/README.md)
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- [Tailscale Official Docs](https://tailscale.com/kb/)
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- [Setup Script](../../tools/setup.sh)
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## Change Log
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### 2025-11-16 - Initial Integration
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- Added Tailscale health monitoring to GraphDone Core
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- Integrated into `tools/setup.sh`
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- Created setup script and documentation
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- Part of core infrastructure capabilities
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---
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**Status**: Production Ready
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**Maintainer**: GraphDone DevOps
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**Related**: GraphDone-Devops/monitoring/tailscale

‎scripts/setup-tailscale-monitor.sh‎

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#!/bin/bash
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# Setup Tailscale Health Monitoring for GraphDone Core
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# Ensures Tailscale auto-recovers from freezes/hangs
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set -euo pipefail
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SCRIPT_DIR="$(cd "$(dirname "${BASH_SOURCE[0]}")" && pwd)"
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# Colors
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GREEN='\033[0;32m'
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YELLOW='\033[1;33m'
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BLUE='\033[0;34m'
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NC='\033[0m'
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echo -e "${GREEN}━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━${NC}"
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echo -e "${GREEN} GraphDone Core - Tailscale Health Monitor Setup${NC}"
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echo -e "${GREEN}━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━${NC}"
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echo ""
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# Step 1: Create health monitor script
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echo -e "${YELLOW}Step 1/4: Creating Tailscale health monitor script...${NC}"
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sudo tee /usr/local/bin/tailscale-health-monitor.sh > /dev/null << 'EOF'
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#!/bin/bash
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# Tailscale Health Monitor - Auto-restart on freeze
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# Part of GraphDone Core infrastructure
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LOG_FILE="/var/log/tailscale-health.log"
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TIMEOUT=5
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log() {
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echo "[$(date '+%Y-%m-%d %H:%M:%S')] $1" | tee -a "$LOG_FILE"
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}
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check_tailscale() {
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if timeout $TIMEOUT tailscale status > /dev/null 2>&1; then
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return 0
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else
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return 1
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fi
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}
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log "Starting Tailscale health check (GraphDone Core)..."
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if check_tailscale; then
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log "✓ Tailscale is healthy"
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exit 0
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else
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log "✗ Tailscale is frozen or unresponsive"
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log "Restarting tailscaled service..."
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systemctl restart tailscaled
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sleep 3
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if check_tailscale; then
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log "✓ Tailscale successfully restarted"
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exit 0
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else
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log "✗ Tailscale restart failed - manual intervention needed"
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exit 1
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fi
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fi
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EOF
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sudo chmod +x /usr/local/bin/tailscale-health-monitor.sh
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echo -e "${BLUE}✓${NC} Created health monitor script"
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# Step 2: Create systemd service
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echo -e "${YELLOW}Step 2/4: Creating systemd service...${NC}"
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sudo tee /etc/systemd/system/tailscale-health-monitor.service > /dev/null << 'EOF'
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[Unit]
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Description=Tailscale Health Monitor (GraphDone Core)
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After=tailscaled.service
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Documentation=https://github.com/graphdone/graphdone-core
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[Service]
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Type=oneshot
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ExecStart=/usr/local/bin/tailscale-health-monitor.sh
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StandardOutput=journal
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StandardError=journal
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User=root
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[Install]
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WantedBy=multi-user.target
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EOF
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echo -e "${BLUE}✓${NC} Created systemd service"
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# Step 3: Create systemd timer
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echo -e "${YELLOW}Step 3/4: Creating systemd timer...${NC}"
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sudo tee /etc/systemd/system/tailscale-health-monitor.timer > /dev/null << 'EOF'
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[Unit]
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Description=Tailscale Health Monitor Timer (GraphDone Core)
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Requires=tailscale-health-monitor.service
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Documentation=https://github.com/graphdone/graphdone-core
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[Timer]
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# Run 2 minutes after boot
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OnBootSec=2min
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# Then every 5 minutes
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OnUnitActiveSec=5min
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# Precise timing
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AccuracySec=1s
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Persistent=true
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[Install]
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WantedBy=timers.target
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EOF
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echo -e "${BLUE}✓${NC} Created systemd timer"
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# Step 4: Enable and start timer
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echo -e "${YELLOW}Step 4/4: Enabling and starting timer...${NC}"
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sudo systemctl daemon-reload
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sudo systemctl enable tailscale-health-monitor.timer
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sudo systemctl start tailscale-health-monitor.timer
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echo -e "${BLUE}✓${NC} Timer enabled and started"
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# Verify installation
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echo ""
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echo -e "${GREEN}━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━${NC}"
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echo -e "${GREEN} Installation Complete${NC}"
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echo -e "${GREEN}━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━${NC}"
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echo ""
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echo "Verification:"
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sudo systemctl status tailscale-health-monitor.timer --no-pager | head -10
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echo ""
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echo "Log file: /var/log/tailscale-health.log"
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echo "Next check: $(systemctl list-timers tailscale-health-monitor.timer --no-pager | grep tailscale)"
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echo ""
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echo -e "${GREEN}✓ Tailscale health monitoring is now active for GraphDone Core${NC}"

‎tools/setup.sh‎

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echo "🏗️ Building all packages..."
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npm run build
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# Setup Tailscale health monitoring (if Tailscale is installed)
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if command -v tailscale &> /dev/null; then
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echo "🔧 Setting up Tailscale health monitoring..."
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SCRIPT_DIR="$(cd "$(dirname "${BASH_SOURCE[0]}")" && pwd)"
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if [ -f "$SCRIPT_DIR/../scripts/setup-tailscale-monitor.sh" ]; then
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if sudo -n true 2>/dev/null; then
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bash "$SCRIPT_DIR/../scripts/setup-tailscale-monitor.sh"
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else
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echo "⚠️ Tailscale monitoring requires sudo. Run manually:"
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echo " sudo bash $SCRIPT_DIR/../scripts/setup-tailscale-monitor.sh"
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fi
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fi
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else
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echo "ℹ️ Tailscale not installed - skipping health monitoring setup"
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echo " (Install Tailscale and run: sudo bash ./scripts/setup-tailscale-monitor.sh)"
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fi
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echo "✅ Setup complete!"
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echo ""
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