I have the same Problem on Ubuntu Server 20.04.1 Release.
I followed the Post-Installation-Steps from
https://help.ubuntu.com/community/Full_Disk_Encryption_Howto_2019.
If you add the Keyfile for the root-Partition to /etc/crypttab and
update the initramfs, it will Warn with th above said warning:
WARNING: Skipping root target md1_crypt: uses a key file
On a reboot, the initramfs does not even ask for a password anymore, it
just fails.
Very weird that we seem to be the only people on the internet having
this problem.
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https://bugs.launchpad.net/bugs/1879146
Title:
Cryptsetup ignoring KEYFILE_PATTERN
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