Please can you provide as much information as you have? For example, "the ctl status is failed 255" is clearly a paraphrase of something that you're seeing; it would be more useful if you could please copy and paste the original text of the error messages.
Forum research is probably leading you up entirely the wrong path; that sounds like information that predates systemd. The ssh.service unit has "After=network.target". "journalctl -u sshd" won't find anything because that's not what the unit is called. Try "journalctl -u ssh". ** Changed in: openssh (Ubuntu) Status: New => Incomplete -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/1549473 Title: ssh will not start at boot: systemctl status ssh -> output is listed as failed 255. To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/1549473/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs