Firstly, me too, this is super annoying. As a rule of thumb any
'feature' that *requires* the user to drop to CLI to put in regular
manual commands *to keep the system secure and updated* ... in a desktop
/ consumer OS... is a bug.

It seems there are separate issues here that could be addressed
separately:

1. the auto setup does not intelligently ask/warn about its default of
setting up a very small /boot

2. there exists no user-friendly auto cleanup for the things clogging up
/boot

3. the /boot does not have any elegant way of automatically (or via a
setting) "overflowing" into the (usually abundant) storage space outside
of /boot for its old kernel data etc

4. when the "full, cannot update any more" problem occurs, there is no
useful feedback or suggestion or wizard from the OS for the user... just
essentially a FU message.

5. apparently there is not an "easy" way to resize /boot to allow more
crap to accumulate and thus postpone the problem... if there *is* an
easy way then see (4) it should be provided then and there to the user;
if there is *not* an easy way then this proves the point that this is
not a trivial bug.

Addressing at least one of these would help the problem, and all could
be worked on.

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https://bugs.launchpad.net/bugs/1357093

Title:
  LVM or Encrypted install creates too small /boot partition

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