I haven't been able to test this since the systems I have here don't
have any kernel images lying around, but wondering if this patch could
help narrow down the cause?

Apply to a (copy) of /usr/bin/unattended-upgrade - possibly put in
/usr/local/bin/ so it is called before the package-installed version
(don't forget to clear the bash hash cache ("hash -r") first)

Then:

sudo /usr/local/bin/unattended-upgrade --verbose --debug

** Patch added: "Kernel pkg debugging"
   
https://bugs.launchpad.net/ubuntu/+source/apt/+bug/1914278/+attachment/5459187/+files/kernel-pkg-debug.patch

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https://bugs.launchpad.net/bugs/1914278

Title:
  apt autoremove is not removing unused kernels

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