I thought of a further edge case:

8. What happens if reimaging from the OEM image, and then upgrading to
the updates pocket all at once, including the update that triggered this
bug together with this for it? Which postinst will run first? If not
deterministic, and this one runs first, will that cause a problem? Do we
need a Breaks clause for ordering purposes? Or is it OK to remove
/etc/default/grub.d/oem-flavour.cfg _before_ the bug is triggered?

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https://bugs.launchpad.net/bugs/2083657

Title:
  Remove oem-flavour.cfg for the OEM kernel retirement

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