Okay, this is strange. Just for S&G, I tried again with the procedure
described in Daniel T’s answer to my question over at Ask Ubuntu:
https://askubuntu.com/a/1566464/1773099 I realized that something I’d
missed when I did this before (when the procedure failed to get os-
prober working again) was that I’d forgotten to regenerate the
bootloader. (See the three lines under “Regenerate bootloader in case
it's corrupt”.) So, I once again disabled os-prober in
/etc/default/grub, ran update-grub, reinstalled the new kernel packages,
_regenerated the bootloader,_ restarted the computer, then re-enabled
os-prober in /etc/default/grub, ran “sudo update-grub” again, and voila,
os-prober detects the Windows installation and adds it to the list,
exiting without error. So, to recap:

- When I updated to 6.17.0-23-generic, this problem occurred. It was
fixed when doing Daniel T’s procedure, including regenerating the
bootloader.

- When I updated to 6.17.0-29-generic, this problem occurred. It wasn’t
fixed when doing Daniel T’s procedure, but that might have to do with
the fact that I omitted regenerating the bootloader.

- Finally I did Daniel T’s procedure again, including regenerating the
bootloader. Now os-prober seems to work again.

So, apparently, this bug occurs _every time the kernel is updated,_ but
not every time os-prober is run. I guess we’ll see if it happens again
on the next kernel update. I’m still hoping we can fix this (it’s
annoying to have to do all that mess on every kernel update, and I’m
worried about what state the computer is left in when os-prober hangs
during a kernel update), but at least os-prober is working again for now
(fingers crossed).

Oh, and one last note: since I’m talking so much about “Daniel T’s
procedure” I should note a few things I did differently (from what he
wrote) every time I did his procedure. First, I omitted “sudo -i”,
preferring just to put “sudo” at the front of every command (I didn’t
want to risk leaving a terminal window open with root access). Second, I
didn’t bother with the “Free up space” line, instead going straight from
“sudo apt --fix-broken install” to “apt reinstall…” (etc). Finally, I
didn’t bother with the lines under “Reactivate metapackage” and “Update
to 24.04.4”; I already have the kernel metapackage linux-generic-
hwe-24.04 installed, and it turns out I was already using 24.04.4 (I had
mistakenly given him the impression that I was using 24.04.1, because of
something I saw when running “uname -r,” when I should’ve been looking
in e.g. the About screen of the Settings app). Anyway, none of this
probably matters, but because I’m being so detail-oriented with this
report I thought I should probably note all this!)

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https://bugs.launchpad.net/bugs/2153501

Title:
  os-prober hangs on update-grub or kernel update

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