Milan: Thanks for your response, but that doesn't solve my problem.
First, I have newer Grub version, with no menu.lst (grub.cfg takes its
place). Second, my Grub config files DO get updated after a new kernel
upgrade, but in a way I don't like. That is, new entries are added to
Grub boot menu ALONGSIDE the existing ones, instead of REPLACING the
older entries.

For example, after the recent kernel upgrade from version 2.6.31-20 to
2.6.31-21, I ended up with both of these kernels being available in the
Grub menu. Then I had to uninstall the older version (image and headers)
manually to save disk space (~150 MB).

The behavior I'd like to have, is an older kernel automatically being
replaced by the upgrade, so that I don't have to perform any additional
steps. It all boils down to having selected a wrong option ("keep the
local version currently installed") when I was upgrading kernel for the
FIRST time. It was a stupid mistake which I don't know how to correct
and can't find any information about...

-- 
[MASTER] Grub does not update menu.lst when it was hand-edited (so it defaults 
to old 2.6.28 kernel after upgrade to ubuntu 9.10 from 9.04): add 'help' 
details to debconf prompt
https://bugs.launchpad.net/bugs/470490
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