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update-grub does get run by grub-* packages during postinst
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Packages in question:

The postinst script of these packages should call update-grub. Otherwise these packages have no effect before a kernel upgrade triggers or the user manually runs it.

Debian has no update-grub trigger yet:




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Done for grub-screen-resolution package...
run update-grub during postinst so package takes effect right after installation -

Can be easily replicated for the grub-enable-apparmor and #grub-verbose-output package. Just waiting for potential comments on this.

Anyone has any suggestions on the error message when this fails? (@bnvk, @mfc, @MemoryLost)

'update-grub' failed with exit code $?. $DPKG_MAINTSCRIPT_PACKAGE is most \
likely only the trigger, not the cause. Unless you know this is not an issue, \
you should fix running 'update-grub', otherwise your system might no longer \
boot." >&2

(It fails open, i.e. package installation will succeed. It's just supposed to be a warning in case this fails.)