The Hidden Linux Routing Issue That Broke My Deployment

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 DNS resolution, verified firewall rules, confirmed that Caddy was listening on the expected ports, and made sure the application itself was reachable. Every check came back clean. That was the first clue that the problem might not be where the logs were pointing. The Obvious Things The first assumption was DNS. I verified that the domain resolved to the correct public IP. dig +short my-domain.com Everything looked correct. Next came the firewall. sudo ufw status Ports 80 and 443 were open. There were no unexpected deny rules, and nothing suggested inbound traffic was being blocked. Then I checked whether Caddy was actually listening. sudo ss -tulpn | grep -E ':80|:443' Again, everything looked normal. The application itself was healthy too. curl http://localhost:3001 returned a valid response. At this point I had checked most of the things engineers typically check when certificate validation fails. DNS looked good, the firewall looked good, the reverse proxy was healthy, and the application was running. Yet the validation errors continued. The Part That Sent Me In The Wrong Direction The error messages kept mentioning connectivity problems and possible firewall issues. That wording influenced my thinking more than it should have. I spent time investigating firewall rules, reverse proxy configuration, TLS settings, and domain configuration. Every new hypothesis felt reasonable, but none of them explained why local tests consistently succeeded while external validation continued