I fixed this in zesty but forgot to reference the bug.
ubuntu-release-upgrader (1:17.04.4) zesty; urgency=medium
* DistUpgrade/DistUpgradeCache.py: when checking for free space in boot also
check for kernels being upgraded not just installed.
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https://bugs.launchpad.net/bugs/1640645
Title:
free space check doesn't take into account kernel upgrades
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