I've had to move the initrd's elsewhere when they've filled up /boot as well. Move all but one in use and deleting to where ever you have space, delete the linux-images gracefully with apt, moving another back when deleting it next.

Anymore I give boot a 500mb-1g boot drive because kernels are getting huge, I got tired of breaking things with 100-200mb /boot drives across time.

-mb

Move the old initrds to somewhere that has more space, then reboot and see if anything breaks? dpkg saying that the files are not owned by anything sounds reasonable if they're built dynamically.

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