@ahasenack, I found this post (took plenty of Google foo) but it was helpful.
For anyone else, 18.04 LTS STILL has this issue. The following fixed it: After=network-online.target Wants=network-online.target These are in my [Unit] section at the top of /etc/systemd/system/sshd.service <code_paste_from_service_file> [Unit] Description=OpenBSD Secure Shell server After=network-online.target auditd.service Wants=network-online.target ConditionPathExists=!/etc/ssh/sshd_not_to_be_run [Service] </code_paste_from_service_file> I hope this is helpful to others! -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to the bug report. https://bugs.launchpad.net/bugs/216847 Title: sshd will not start at boot if ListenAddress is set, because network interface is not yet up To manage notifications about this bug go to: https://bugs.launchpad.net/openssh/+bug/216847/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs