I also experienced the same problem upgrading Gutsy to Hardy. I realise
that Gutsy is no longer supported, but I mean to verify that this bug
does exist and it's not just you Daniel.

http://ubuntuforums.org/showthread.php?t=1153754

Gutsy is a guest inside Windows Server 2008 hyper-v.

I run sudo apt-get update and sudo apt-get upgrade

This notes that:
The following packages have been kept back:
linux-headers-generic linux-image-generic linux-restricted-modules-generic
0 upgraded, 0 newly installed, 0 to remove and 3 not upgraded.

I edited grub's menu.lst to boot into kernel version 2.6.22-14-generic
(because of the bug with 2.6.22-15-generic - see
https://help.ubuntu.com/community/Ha...own%20Problems )

and then rebooted into 2.6.22-14-generic to run the upgrade.

and so it just quits on me after I press y and enter as described.

cat /var/log/dist-upgrade/main.log
2009-12-25 00:26:18,622 INFO release-upgrader version '0.87.30' started
2009-12-25 00:26:18,629 DEBUG Using 'DistUpgradeViewText' view
2009-12-25 00:26:18,726 DEBUG enable dpkg --force-overwrite
2009-12-25 00:26:18,804 DEBUG lsb-release: 'gutsy'


I eventually fixed it by editing /etc/environment, removing LANG="en_AU.UTF-8" 
and adding 

LANGUAGE=C
LANG=C

at the start of the file, then restarting.

-- 
do-release-upgrade does not start with locale bg_BG.UTF-8 in 8.10
https://bugs.launchpad.net/bugs/389388
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