Ok, basically if I reboot the server caddy will try to reload, here the error when running journalctl -xeu caddy.service --no-pager
Dec 11 15:28:54 webarto-server systemd[1]: Starting Caddy...
░░ Subject: A start job for unit caddy.service has begun execution
░░ Defined-By: systemd
░░ Support: https://access.redhat.com/support
░░
░░ A start job for unit caddy.service has begun execution.
░░
░░ The job identifier is 235.
Dec 11 15:28:54 webarto-server caddy[784]: caddy.HomeDir=/var/lib/caddy
Dec 11 15:28:54 webarto-server caddy[784]: caddy.AppDataDir=/var/lib/caddy/.local/share/caddy
Dec 11 15:28:54 webarto-server caddy[784]: caddy.AppConfigDir=/var/lib/caddy/.config/caddy
Dec 11 15:28:54 webarto-server caddy[784]: caddy.ConfigAutosavePath=/var/lib/caddy/.config/caddy/autosave.json
Dec 11 15:28:54 webarto-server caddy[784]: caddy.Version=v2.7.6 h1:w0NymbG2m9PcvKWsrXO6EEkY9Ru4FJK8uQbYcev1p3A=
Dec 11 15:28:54 webarto-server caddy[784]: runtime.GOOS=linux
Dec 11 15:28:54 webarto-server caddy[784]: runtime.GOARCH=amd64
Dec 11 15:28:54 webarto-server caddy[784]: runtime.Compiler=gc
Dec 11 15:28:54 webarto-server caddy[784]: runtime.NumCPU=4
Dec 11 15:28:54 webarto-server caddy[784]: runtime.GOMAXPROCS=4
Dec 11 15:28:54 webarto-server caddy[784]: runtime.Version=go1.20.10
Dec 11 15:28:54 webarto-server caddy[784]: os.Getwd=/
Dec 11 15:28:54 webarto-server caddy[784]: LANG=en_US.UTF-8
Dec 11 15:28:54 webarto-server caddy[784]: PATH=/usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin
Dec 11 15:28:54 webarto-server caddy[784]: NOTIFY_SOCKET=/run/systemd/notify
Dec 11 15:28:54 webarto-server caddy[784]: HOME=/var/lib/caddy
Dec 11 15:28:54 webarto-server caddy[784]: LOGNAME=caddy
Dec 11 15:28:54 webarto-server caddy[784]: USER=caddy
Dec 11 15:28:54 webarto-server caddy[784]: INVOCATION_ID=d02e72ad6517492094888d309829a91e
Dec 11 15:28:54 webarto-server caddy[784]: JOURNAL_STREAM=8:17586
Dec 11 15:28:54 webarto-server caddy[784]: SYSTEMD_EXEC_PID=784
Dec 11 15:28:54 webarto-server caddy[784]: {"level":"info","ts":1702308534.6135402,"msg":"using provided configuration","config_file":"/etc/caddy/Caddyfile","config_adapter":""}
Dec 11 15:28:54 webarto-server caddy[784]: {"level":"info","ts":1702308534.6172988,"logger":"admin","msg":"admin endpoint started","address":"localhost:2019","enforce_origin":false,"origins":["//127.0.0.1:2019","//localhost:2019","//[::1]:2019"]}
Dec 11 15:28:54 webarto-server caddy[784]: {"level":"info","ts":1702308534.6182199,"logger":"http.auto_https","msg":"server is listening only on the HTTPS port but has no TLS connection policies; adding one to enable TLS","server_name":"srv0","https_port":443}
Dec 11 15:28:54 webarto-server caddy[784]: {"level":"info","ts":1702308534.6183107,"logger":"http.auto_https","msg":"enabling automatic HTTP->HTTPS redirects","server_name":"srv0"}
Dec 11 15:28:54 webarto-server caddy[784]: {"level":"info","ts":1702308534.6194887,"logger":"tls.cache.maintenance","msg":"started background certificate maintenance","cache":"0xc00010ea80"}
Dec 11 15:28:54 webarto-server caddy[784]: {"level":"info","ts":1702308534.6208663,"logger":"http","msg":"enabling HTTP/3 listener","addr":":443"}
Dec 11 15:28:54 webarto-server caddy[784]: {"level":"info","ts":1702308534.6224236,"logger":"http.log","msg":"server running","name":"srv0","protocols":["h1","h2","h3"]}
Dec 11 15:28:54 webarto-server caddy[784]: {"level":"info","ts":1702308534.6227007,"logger":"http.log","msg":"server running","name":"remaining_auto_https_redirects","protocols":["h1","h2","h3"]}
Dec 11 15:28:54 webarto-server caddy[784]: {"level":"info","ts":1702308534.6228032,"logger":"http","msg":"enabling automatic TLS certificate management","domains":["mydashboard.webarto.co.uk","mattheweyles.art","www.mattheweyles.art","brianburton.art","www.brianburton.art"]}
Dec 11 15:28:54 webarto-server caddy[784]: {"level":"warn","ts":1702308534.6246464,"logger":"tls","msg":"storage cleaning happened too recently; skipping for now","storage":"FileStorage:/var/lib/caddy/.local/share/caddy","instance":"966c2002-5baa-4962-9536-3f4d8b4bb0af","try_again":1702394934.6246445,"try_again_in":86399.999999569}
Dec 11 15:28:54 webarto-server caddy[784]: {"level":"info","ts":1702308534.6247573,"logger":"tls","msg":"finished cleaning storage units"}
Dec 11 15:29:24 webarto-server caddy[784]: {"level":"warn","ts":1702308564.6274936,"logger":"tls","msg":"stapling OCSP","error":"no OCSP stapling for [mydashboard.webarto.co.uk]: making OCSP request: Post \"http://r3.o.lencr.org\": dial tcp 62.115.253.187:80: i/o timeout","identifiers":["mydashboard.webarto.co.uk"]}
Dec 11 15:29:54 webarto-server caddy[784]: {"level":"warn","ts":1702308594.6309583,"logger":"tls","msg":"stapling OCSP","error":"no OCSP stapling for [mattheweyles.art]: making OCSP request: Post \"http://r3.o.lencr.org\": dial tcp [2001:2030:21::3e73:fc68]:80: i/o timeout","identifiers":["mattheweyles.art"]}
Dec 11 15:30:24 webarto-server systemd[1]: caddy.service: start operation timed out. Terminating.
Dec 11 15:30:24 webarto-server caddy[784]: {"level":"info","ts":1702308624.299674,"msg":"shutting down apps, then terminating","signal":"SIGTERM"}
Dec 11 15:30:24 webarto-server caddy[784]: {"level":"warn","ts":1702308624.300021,"msg":"exiting; byeee!! 👋","signal":"SIGTERM"}
Dec 11 15:30:24 webarto-server caddy[784]: {"level":"warn","ts":1702308624.6338496,"logger":"tls","msg":"stapling OCSP","error":"no OCSP stapling for [www.mattheweyles.art]: making OCSP request: Post \"http://r3.o.lencr.org\": dial tcp [2001:2030:21::3e73:fc68]:80: i/o timeout","identifiers":["www.mattheweyles.art"]}
Dec 11 15:30:29 webarto-server systemd[1]: caddy.service: State 'stop-sigterm' timed out. Killing.
Dec 11 15:30:29 webarto-server systemd[1]: caddy.service: Killing process 784 (caddy) with signal SIGKILL.
Dec 11 15:30:29 webarto-server systemd[1]: caddy.service: Killing process 834 (n/a) with signal SIGKILL.
Dec 11 15:30:29 webarto-server systemd[1]: caddy.service: Killing process 835 (n/a) with signal SIGKILL.
Dec 11 15:30:29 webarto-server systemd[1]: caddy.service: Killing process 839 (n/a) with signal SIGKILL.
Dec 11 15:30:29 webarto-server systemd[1]: caddy.service: Killing process 1017 (caddy) with signal SIGKILL.
Dec 11 15:30:29 webarto-server systemd[1]: caddy.service: Killing process 1019 (n/a) with signal SIGKILL.
Dec 11 15:30:29 webarto-server systemd[1]: caddy.service: Main process exited, code=killed, status=9/KILL
░░ Subject: Unit process exited
░░ Defined-By: systemd
░░ Support: https://access.redhat.com/support
░░
░░ An ExecStart= process belonging to unit caddy.service has exited.
░░
░░ The process' exit code is 'killed' and its exit status is 9.
Dec 11 15:30:29 webarto-server systemd[1]: caddy.service: Failed with result 'timeout'.
░░ Subject: Unit failed
░░ Defined-By: systemd
░░ Support: https://access.redhat.com/support
░░
░░ The unit caddy.service has entered the 'failed' state with result 'timeout'.
Dec 11 15:30:29 webarto-server systemd[1]: Failed to start Caddy.
░░ Subject: A start job for unit caddy.service has failed
░░ Defined-By: systemd
░░ Support: https://access.redhat.com/support
░░
░░ A start job for unit caddy.service has finished with a failure.
░░
░░ The job identifier is 235 and the job result is failed.
Dec 11 15:31:39 webarto-server systemd[1]: Starting Caddy...
░░ Subject: A start job for unit caddy.service has begun execution
░░ Defined-By: systemd
░░ Support: https://access.redhat.com/support
░░
░░ A start job for unit caddy.service has begun execution.
░░
░░ The job identifier is 731.
Dec 11 15:31:39 webarto-server caddy[1457]: caddy.HomeDir=/var/lib/caddy
Dec 11 15:31:39 webarto-server caddy[1457]: caddy.AppDataDir=/var/lib/caddy/.local/share/caddy
Dec 11 15:31:39 webarto-server caddy[1457]: caddy.AppConfigDir=/var/lib/caddy/.config/caddy
Dec 11 15:31:39 webarto-server caddy[1457]: caddy.ConfigAutosavePath=/var/lib/caddy/.config/caddy/autosave.json
Dec 11 15:31:39 webarto-server caddy[1457]: caddy.Version=v2.7.6 h1:w0NymbG2m9PcvKWsrXO6EEkY9Ru4FJK8uQbYcev1p3A=
Dec 11 15:31:39 webarto-server caddy[1457]: runtime.GOOS=linux
Dec 11 15:31:39 webarto-server caddy[1457]: runtime.GOARCH=amd64
Dec 11 15:31:39 webarto-server caddy[1457]: runtime.Compiler=gc
Dec 11 15:31:39 webarto-server caddy[1457]: runtime.NumCPU=4
Dec 11 15:31:39 webarto-server caddy[1457]: runtime.GOMAXPROCS=4
Dec 11 15:31:39 webarto-server caddy[1457]: runtime.Version=go1.20.10
Dec 11 15:31:39 webarto-server caddy[1457]: os.Getwd=/
Dec 11 15:31:39 webarto-server caddy[1457]: LANG=en_US.UTF-8
Dec 11 15:31:39 webarto-server caddy[1457]: PATH=/usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin
Dec 11 15:31:39 webarto-server caddy[1457]: NOTIFY_SOCKET=/run/systemd/notify
Dec 11 15:31:39 webarto-server caddy[1457]: HOME=/var/lib/caddy
Dec 11 15:31:39 webarto-server caddy[1457]: LOGNAME=caddy
Dec 11 15:31:39 webarto-server caddy[1457]: USER=caddy
Dec 11 15:31:39 webarto-server caddy[1457]: INVOCATION_ID=15447e0d279f4cd4a3e1ba710ee6daa1
Dec 11 15:31:39 webarto-server caddy[1457]: JOURNAL_STREAM=8:17334
Dec 11 15:31:39 webarto-server caddy[1457]: SYSTEMD_EXEC_PID=1457
Dec 11 15:31:39 webarto-server caddy[1457]: {"level":"info","ts":1702308699.3535414,"msg":"using provided configuration","config_file":"/etc/caddy/Caddyfile","config_adapter":""}
Dec 11 15:31:39 webarto-server caddy[1457]: {"level":"info","ts":1702308699.355705,"logger":"admin","msg":"admin endpoint started","address":"localhost:2019","enforce_origin":false,"origins":["//localhost:2019","//[::1]:2019","//127.0.0.1:2019"]}
Dec 11 15:31:39 webarto-server caddy[1457]: {"level":"info","ts":1702308699.355884,"logger":"http.auto_https","msg":"server is listening only on the HTTPS port but has no TLS connection policies; adding one to enable TLS","server_name":"srv0","https_port":443}
Dec 11 15:31:39 webarto-server caddy[1457]: {"level":"info","ts":1702308699.3559098,"logger":"http.auto_https","msg":"enabling automatic HTTP->HTTPS redirects","server_name":"srv0"}
Dec 11 15:31:39 webarto-server caddy[1457]: {"level":"info","ts":1702308699.3559415,"logger":"tls.cache.maintenance","msg":"started background certificate maintenance","cache":"0xc0003a8a80"}
Dec 11 15:31:39 webarto-server caddy[1457]: {"level":"info","ts":1702308699.3566704,"logger":"http","msg":"enabling HTTP/3 listener","addr":":443"}
Dec 11 15:31:39 webarto-server caddy[1457]: {"level":"info","ts":1702308699.3568628,"logger":"http.log","msg":"server running","name":"srv0","protocols":["h1","h2","h3"]}
Dec 11 15:31:39 webarto-server caddy[1457]: {"level":"info","ts":1702308699.3569431,"logger":"http.log","msg":"server running","name":"remaining_auto_https_redirects","protocols":["h1","h2","h3"]}
Dec 11 15:31:39 webarto-server caddy[1457]: {"level":"info","ts":1702308699.3569567,"logger":"http","msg":"enabling automatic TLS certificate management","domains":["mydashboard.webarto.co.uk","mattheweyles.art","www.mattheweyles.art","brianburton.art","www.brianburton.art"]}
Dec 11 15:31:39 webarto-server caddy[1457]: {"level":"warn","ts":1702308699.357847,"logger":"tls","msg":"storage cleaning happened too recently; skipping for now","storage":"FileStorage:/var/lib/caddy/.local/share/caddy","instance":"966c2002-5baa-4962-9536-3f4d8b4bb0af","try_again":1702395099.3578458,"try_again_in":86399.999999629}
Dec 11 15:31:39 webarto-server caddy[1457]: {"level":"info","ts":1702308699.3585103,"logger":"tls","msg":"finished cleaning storage units"}
Dec 11 15:32:09 webarto-server caddy[1457]: {"level":"warn","ts":1702308729.3579254,"logger":"tls","msg":"stapling OCSP","error":"no OCSP stapling for [mydashboard.webarto.co.uk]: making OCSP request: Post \"http://r3.o.lencr.org\": dial tcp [2001:2030:21::3e73:fc59]:80: i/o timeout","identifiers":["mydashboard.webarto.co.uk"]}
Dec 11 15:32:39 webarto-server caddy[1457]: {"level":"warn","ts":1702308759.3589654,"logger":"tls","msg":"stapling OCSP","error":"no OCSP stapling for [mattheweyles.art]: making OCSP request: Post \"http://r3.o.lencr.org\": dial tcp [2001:2030:21::3e73:fc68]:80: i/o timeout","identifiers":["mattheweyles.art"]}
Dec 11 15:33:09 webarto-server caddy[1457]: {"level":"warn","ts":1702308789.3601675,"logger":"tls","msg":"stapling OCSP","error":"no OCSP stapling for [www.mattheweyles.art]: making OCSP request: Post \"http://r3.o.lencr.org\": dial tcp [2001:2030:21::3e73:fc59]:80: i/o timeout","identifiers":["www.mattheweyles.art"]}
Dec 11 15:33:09 webarto-server systemd[1]: caddy.service: start operation timed out. Terminating.
Dec 11 15:33:09 webarto-server caddy[1457]: {"level":"info","ts":1702308789.5476334,"msg":"shutting down apps, then terminating","signal":"SIGTERM"}
Dec 11 15:33:09 webarto-server caddy[1457]: {"level":"warn","ts":1702308789.5477512,"msg":"exiting; byeee!! 👋","signal":"SIGTERM"}
Dec 11 15:33:14 webarto-server systemd[1]: caddy.service: State 'stop-sigterm' timed out. Killing.
Dec 11 15:33:14 webarto-server systemd[1]: caddy.service: Killing process 1457 (caddy) with signal SIGKILL.
Dec 11 15:33:14 webarto-server systemd[1]: caddy.service: Killing process 1461 (caddy) with signal SIGKILL.
Dec 11 15:33:14 webarto-server systemd[1]: caddy.service: Killing process 1462 (caddy) with signal SIGKILL.
Dec 11 15:33:14 webarto-server systemd[1]: caddy.service: Killing process 1463 (n/a) with signal SIGKILL.
Dec 11 15:33:14 webarto-server systemd[1]: caddy.service: Main process exited, code=killed, status=9/KILL
░░ Subject: Unit process exited
░░ Defined-By: systemd
░░ Support: https://access.redhat.com/support
░░
░░ An ExecStart= process belonging to unit caddy.service has exited.
░░
░░ The process' exit code is 'killed' and its exit status is 9.
Dec 11 15:33:14 webarto-server systemd[1]: caddy.service: Failed with result 'timeout'.
░░ Subject: Unit failed
░░ Defined-By: systemd
░░ Support: https://access.redhat.com/support
░░
░░ The unit caddy.service has entered the 'failed' state with result 'timeout'.
Dec 11 15:33:14 webarto-server systemd[1]: Failed to start Caddy.
░░ Subject: A start job for unit caddy.service has failed
░░ Defined-By: systemd
░░ Support: https://access.redhat.com/support
░░
░░ A start job for unit caddy.service has finished with a failure.
░░
░░ The job identifier is 731 and the job result is failed.
This is happening using the current Caddyfile I showed in my previous messages.