Hi.
I'm affected by this issue as well. I have a few virtual machines on which certificates stopped renewing. All machines have Debian Stable with the most recent updates installed as soon as possible. It seems to be an issue with systemd. The following output is on "broken" system: # systemctl list-timers --all NEXT LEFT LAST PASSED UNIT ACTIVATES Fri 2019-03-08 13:31:33 CET 17min left Thu 2019-03-07 13:31:33 CET 23h ago systemd-tmpfiles-clean.timer systemd-tmpfiles-clean.service Fri 2019-03-08 16:59:19 CET 3h 45min left Thu 2019-03-07 21:10:33 CET 16h ago apt-daily.timer apt-daily.service Sat 2019-03-09 06:46:22 CET 17h left Fri 2019-03-08 06:19:33 CET 6h ago apt-daily-upgrade.timer apt-daily-upgrade.service n/a n/a Mon 2019-02-04 12:21:02 CET 1 months 1 days ago certbot.timer certbot.service I tried to run systemctl daemon-reload, but it doesn't help. However, rebooting the machine fixed the issue, at least for some time: # systemctl list-timers --all NEXT LEFT LAST PASSED UNIT ACTIVATES Fri 2019-03-08 14:07:46 CET 52min left Thu 2019-03-07 14:07:46 CET 23h ago systemd-tmpfiles-clean.timer systemd-tmpfiles-clean.service Fri 2019-03-08 18:27:06 CET 5h 12min left Fri 2019-03-08 04:43:46 CET 8h ago certbot.timer certbot.service Sat 2019-03-09 05:08:12 CET 15h left Fri 2019-03-08 13:09:49 CET 5min ago apt-daily.timer apt-daily.service Sat 2019-03-09 06:38:08 CET 17h left Fri 2019-03-08 06:03:49 CET 7h ago apt-daily-upgrade.timer apt-daily-upgrade.service It is quite a huge problem on production when one cannot rely on correct behavior of systemd. -- Marcel Šebek