The Hidden Linux Routing Issue That Broke My Deployment (opens in new tab)

The deployment should have taken a few minutes. The application was running, DNS was configured correctly, and the domain was already pointing to the server's public IP. Caddy was configured as a reverse proxy and was listening on ports 80 and 443. Every item on my deployment checklist appeared healthy. Yet every Let's Encrypt validation attempt kept failing. The error looked simple enough: authorization failed timeout during connect likely firewall problem At first, I believed it. I checked ...