Hi trent - i am interested in this approach: i see you are binding msmtp over /usr/sbin/sendmail - i dont understand how this would lead to a different outcome: how else does msmtp know where to send the mail? is there some implicit assumption about local delivery here? i tried testing but msmtp does not work at all out of the box for me - complains that it has no configuration file)
As far as i can tell, the issue isn't with the "send mail" part, but the part where the mta (exim/postfix) tries to deliver it (returning to logcheck - id agree with losing the 'reboot' mail - it's pretty clear from the log message that the system has been rebooted, so not sure what value this is even under cron. I'd suggest adding Persistent=true in the .timer's [Timer] so that it runs after a resuming from suspend. Perhaps set it to skip if on battery too )
