Walter,

This recipe should permit reproducing the crashes from your intrepid
system; if you can confirm this to be the case, we can go from there on
trying to get debugging information out of it.

$ sudo chroot /media/disk su <username>
$ sudo -s

where <username> is the name of your admin user on the Ubuntu 8.10
install.

That will let us see if sudo is crashing within the 8.10 installation.

-- 
silent login/gdm failures and sudo segfaults with smbpasswd enabled
https://bugs.launchpad.net/bugs/292791
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