@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!

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https://bugs.launchpad.net/bugs/216847

Title:
  sshd will not start at boot if ListenAddress is set, because network
  interface is not yet up

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