Hmm.
Between the last restart and the new shutdown, I only find these two in the logs that indicate that something is off:
chown: cannot access '/usr/share/man/man1/mailq.1.gz': No such file or directory
This one probably has nothing to do with the issue.
The other one seems to point in the same direction as the Watchdog log:
Jul 5 14:59:58 37d337978fcc postfix/master[385]: warning: unix_trigger_event: read timeout for service private/tlsmgr
Everything else reads like business as usual.
So for some reason (too many timeouts), Watchdog requests Postfix to restart but that doesn’t work. To me, the most important question right now is: why?
Obviously, those timeouts need to be addressed as well, but I do have a suspicion: My server is having performance issues at the moment due to insufficient storage speed. So this slows everything down. I am on it, but it will take a bit.
In the meantime, if I could make sure that Postfix comes back up after shutting down, this would help a lot.