apt full-upgrade takes care of this
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This is one of the reasons why I don't use a separate partition for /boot anymore. As I understand it, a separate /boot partition is mostly a legacy thing unless you have an encrypted root partition or some other special setup. For simple cases I recommend having /boot on the root partition to avoid issues like this.
I think that's also the default setup used by the Debian installer if you select Guided partitioning – use entire disk. I'm not 100% sure tho.
Would rec moving them to something more simple, akin to ElementaryOS.
That said, /boot likely isn’t right sized for the number of versions of the kernel required by the bootloader in case of a failure. 512mb-1gb of storage is normally more than enough to handle said copies. As well, apt dist-upgrade will actually remove obsolete packages while apt upgrade does not.
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