Updates

The 2 AM Wake-Up Call # I woke up to find my CI/CD platform had been down for 8 hours. Semaphore, the Ansible automation engine that manages my entire homelab, was stuck in a crash loop: 1 2 3 /usr/local/bin/server-wrapper: line 295: syntax error: unexpected "&&" /usr/local/bin/server-wrapper: line 295: syntax error: unexpected "&&" /usr/local/bin/server-wrapper: line 295: syntax error: unexpected "&&" The same error, repeating every few seconds. The container would start, hit the broken entrypoint script, crash, and restart. Endlessly.

Update, September 2026. Neither Watchtower nor WUD is the current update controller. Both were fully decommissioned in March 2026 after update-related outages; container updates are now Semaphore-managed (safe-update.sh, health-gated with soak and auto-rollback). This post is preserved as the historical migration account — including its NetBox dashboard walk-through, which reflects the IPAM tool of that era, not a current deployment. The Problem # Watchtower had been my go-to for automatic Docker container updates across 8+ services. It worked… mostly. But I kept running into issues: