I've had certbot running on this mailserver that I'm running, and it seems that when the certificate is renewed that Postfix continues to run just fine, but Dovecot starts throwing certificate errors (and blocks iPhone access).
Where do I poke the bear to fix this?
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Well, it would be helpful to actually see some information to work with. "Dovecot starts throwing errors" doesn't help at all. Crystal balls are only a real thing in fiction I'm afraid.
Dovecot doesn't actually start throwing errors, IMAP clients start complaining about expired certificates. I then log in and do a systemctl restart dovecot and the problem goes away.
It appears that Postfix is being restarted, but that Dovecot isn't.
Honestly this last happened in January, and I was really busy at the time so I just restarted it and went on my way. The evidence in /var/log/mail is gone, and there's nothing in the letsencrypt logs about restarting either.
Where would that configuration be?
We're due for a renewal in 6 days, so I can just wait for that to happen to gather log data.
Depends on how you've set you system up to reload Postfix. Did you add a deploy hook to Certbot at time of issuance? Or did you edit the cronjob/systemd timer or did you add your own cronjob/systemd timer?
Deploy hooks can also be found in the corresponding renewal configuration file of the certificates. It would be called renew-hook I believe for some reason though in the file itself
That's just how linux distributions work. They may update versions during the active support window, but usually do not. Essential security releases will get pushed out during the active support and extended windows. Realistically, you shouldn't expect updates on most packages after the release is finalized.
Because of this, the Certbot team initially worked with distributions to fast-track releases - but that was too much work. A few years ago, they dropped direct support for distribution and moved primary support to snapd distribution. The best option to keep certbot up-to date on linux distributions is to use snap.
In terms of renewal, if you upgrade to the most recent version there is a new 'reconfigure' command which should allow you to edit a hook
Certbot, like Ubuntu, has moved to snap apps as their preferred distribution mechanism. I'm not yet willing to install snapd on servers, but it will get you into current versions of Certbot.
If snapd isn't an option (e.g. understandable objections of principle) you can always use the pip instructions (using a virtual environment! as instructed in the Certbot pip documentation).