Upgrading to Debian 13 Trixie

Tue, 12 Aug 2025 07:12:15 -0500

Ah, the trials and tribulations of upgrading Debian 12 Bookworm to Debian 13 Trixie! I learned a valuable lesson this weekend with the update - always read the apt listchanges email. Always.

The upgrade itself went smoothly with no errors during the packages upgrading/installing. I run three main services on my server - nginx, exim, and dovecot. On reboot, all three had issues with the upgraded packages.

nginx

I received the following error in my nginx error.log:

Nginx, OCSP stapling, booting, systemd and Debian 9

Sun, 10 Dec 2017 18:26:24 -0500

Noticed these lines in journalctl when nginx didn’t start after a reboot:

Dec 10 17:43:30 mail1 nginx[3485]: nginx: [warn] "ssl_stapling" ignored, host not found in OCSP responder "ocsp.int-x3.letsencrypt.org" in the certificate "/etc/letsencrypt/live/www.example.com/fullchain.pem"
Dec 10 17:43:30 mail1 nginx[3485]: nginx: [emerg] bind() to [<IPv6 address>]:80 failed (99: Cannot assign requested address)
Dec 10 17:43:30 mail1 nginx[3485]: nginx: configuration file /etc/nginx/nginx.conf test failed
Dec 10 17:43:30 mail1 systemd[1]: nginx.service: Control process exited, code=exited status=1
Dec 10 17:43:30 mail1 systemd[1]: nginx.service: Unit entered failed state.
Dec 10 17:43:30 mail1 systemd[1]: nginx.service: Failed with result 'exit-code'.
Dec 10 17:52:35 mail1 systemd[1]: nginx.service: Failed to read PID from file /run/nginx.pid: Invalid argument

Hmmm…

Debian on The Gnu Pit

Upgrading to Debian 13 Trixie

nginx

Nginx, OCSP stapling, booting, systemd and Debian 9