Did you set GRUB_ENABLE_CRYPTODISK? Please attach your
/etc/default/grub.

Encrypted /boot is not really supported, the installer does not create
it, and no testing is performed on it. You have to hack around things
and add GRUB_ENABLE_CRYPTODISK to /etc/default/grub, so it's very hard
to setup.

Last time I tried encrypted /boot, it would prompt me for password, but
did not actually take any input.

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https://bugs.launchpad.net/bugs/1927857

Title:
  Update to grub 2.04-1ubuntu44 breaks booting

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