There are multiple things that I have identified that prevent quick
boots with systems configured with encrypted swap.

1) resume device is most likely incorrect
Steps to mitigate:
$ echo RESUME=none | sudo tee -a /etc/initramfs-tools/conf.d/resume
$ sudo initramfs-update -u

2) systems, not in fact hanging to boot...

I can reproduce and see the timeouts reliably in the log, but they are
not causing the system to fail to boot and the systems do come up non-
degraged. Specifically eventually during boot and after a few Job
Timeouts, the swap does come up and is activated.

If you experience this, please switch to tty3 and do:
$ systemctl is-system-running
$ systemctl list-units --failed

If that is "running", and no units are listed, all is good. On the
systems I've reproduced the timeout on, they would boot non-degraded
without any failed units.

I wonder if the system is simply still upgrading... for example, I can
see in jibel's logs that e.g. there is a tonne of incomplete upgrades
due to .dpkg-new and .dpkg-tmp files:

Apr 23 08:46:25 ubuntu gnome-session[1567]: (gnome-software:1734): As-WARNING 
**: failed to rescan: Failed to parse 
/usr/share/applications/gnome-sudoku.desktop.dpkg-tmp file: cannot process file 
of type text/plain
Apr 23 08:46:25 ubuntu gnome-session[1567]: (gnome-software:1734): As-WARNING 
**: failed to rescan: Failed to parse 
/usr/share/applications/gnome-sudoku.desktop file: cannot process file of type 
application/x-desktop
Apr 23 08:46:26 ubuntu gnome-session[1567]: (gnome-software:1734): As-WARNING 
**: failed to rescan: Failed to parse 
/usr/share/applications/gnome-system-log.desktop.dpkg-new file: Error opening 
file: Permission denied
Apr 23 08:46:26 ubuntu gnome-session[1567]: (gnome-software:1734): As-WARNING 
**: failed to rescan: Failed to parse 
/usr/share/applications/gnome-system-log.desktop.dpkg-tmp file: cannot process 
file of type text/plain
Apr 23 08:46:26 ubuntu gnome-session[1567]: (gnome-software:1734): As-WARNING 
**: failed to rescan: Failed to parse 
/usr/share/applications/gnome-system-log.desktop file: cannot process file of 
type application/x-desktop
Apr 23 08:46:27 ubuntu gnome-session[1567]: (gnome-software:1734): As-WARNING 
**: failed to rescan: Failed to parse 
/usr/share/applications/gnome-system-monitor-kde.desktop.dpkg-new file: Error 
opening file: Permission denied

And similar.

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https://bugs.launchpad.net/bugs/1765724

Title:
  Xenial -> Bionic - System fails to boot after upgrade - gnome-
  screensaver & gnome-shell fail to start?

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