Earlier quoted context omitted.
Caddy restarts gracefully with zero downtime. If you're killing the process and starting one anew, you're doing it wrong. Use signal USR1 to gracefully apply new configuration changes. Failed reloads fall back to the current working configuration without any changes or downtime. https://caddyserver.com/docs/cli#usr1
This misses the overall point. If I am hosting 5 sites on caddy, and add a 6th one, I restart the server. If the 6th site doesn't work (for example, if DNS didn't resolve for lets encrypt), the other 5 sites which were working before the restart, all fail to start as caddy completely crashes. This is basic resiliency you'd expect from your web server. Why should the other 5 sites fail to start if their configs are co…
No, you don't. You reload the server, not restart it. Restarting a web server should only be required if you get an upgrade for it (or for OpenSSL etc.)