If you struggle with a /boot partition that is too small for updates, and you are too intimidated by the way to resize your /boot partition, there might be an easier fix:

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It is possible to configure a better compression algorithm for the images in /boot. To do this, edit /etc/initramfs-tools/initramfs.conf and change the existing line to

COMPRESS=xz

Then rebuild the images using

sudo update-initramfs -u -k all

If you get an error during the last step, please immediately get help, because otherwise you might have bricked your system.