I've struggled through this several times now. I don't have a definitive
solution but the general routine was something like this. When you asked
to enroll the machine owner key to sign the kernel module there is an
interface that popups up and waits for user input. I tried this in in a
shell-only session and in a gnome session several times. In both cases
the process that spawns the window gets stuck in a child process and I
think it was sent to a different tty altogether. One time I accidentally
recover the interface by killing all the login window session processes
while I was in a trying something else in a shell session. When i jumped
back everything redrew and there was a new window that asked me to
enroll the MOK key password.

I was not able to reproduce that the next time I got stuck in this spot,
but what worked for me was disabling my machines nvidia video card
proprietary drivers, and then switching from wayland to gnome (or gnome
to wayland) after I did that then the processes worked as it was
supposed to.

This issue is very frustrating, but you should be able to keep secure
boot enabled.  I saved the logs from those times I was able to get it to
work. I'll see if I can find anything to back up what I'm saying here.

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https://bugs.launchpad.net/bugs/1775672

Title:
  virtualbox-dkms installation hangs in 18.04 (with secure boot)

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