So summing up my previous comment, there are actually two problems here:

1. When a new kernel is installed, grub config is NOT updated
accordingly (see point 3 in previous comment).

2. There seem to be different mechanisms to generate initrd.img. And at
least one of them runs automatically and fails to generate a proper
initrd. Manually generating it with "dracut --force" generates a working
initrd.

I guess, this problem is related to the transition from initramfs-tools
to dracut.

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https://bugs.launchpad.net/bugs/2162931

Title:
  LUKS crypted root can not be opened during initrd

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