I have essentially the same bug.  I am running a 64-bit installation of
Karmic.  Every time I update a kernel via Update Manager -- it's
happened three times now -- I am given the usual message to reboot my
machine.  But grub2 does not automatically update.  I have to run
update-grub manually.  Then it works.

I have a very similar installation of Karmic on another computer, except
that it is 32-bit.  There, grub2 updates itself just fine on kernel
updates.

Differences in the two installations aside from 32- vs. 64-bit that come
to mind are: the 32-bit one (that updates grub2) runs on an ext4 file
system, while the 64-bit one that doesn't update runs ext3; and the
32-bit installation was clean, while the 64-bit one was reinstalled
after a failed upgrade from Jaunty but without partitioning.  (It seems
to run fine except for one other current strangeness, though, that I
believe to be unrelated.)

-- 
Installed 2.6.31-10.31 kernel not on menu
https://bugs.launchpad.net/bugs/427679
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