I have booted from the livecd and chrooted into the broken system, the kernel 
package is listed as installed but grub is unable to find it:
[EMAIL PROTECTED]:/# sudo update-grub
sudo: unable to resolve host ubuntu
Searching for GRUB installation directory ... found: /boot/grub
findfs: Unable to resolve 'UUID=4f99a04d-379f-43fd-86c6-a1ba3b9cb8e2'
Cannot determine root device.  Assuming /dev/hda1
This error is probably caused by an invalid /etc/fstab
Searching for default file ... found: /boot/grub/default
Testing for an existing GRUB menu.lst file ... found: /boot/grub/menu.lst
Searching for splash image ... none found, skipping ...
Found kernel: /boot/vmlinuz-2.6.24-21-generic
Found kernel: /boot/vmlinuz-2.6.24-19-generic
Found kernel: /boot/memtest86+.bin
Updating /boot/grub/menu.lst ... done

[EMAIL PROTECTED]:/# dpkg -l | grep -i linux-image
ii  linux-image-2.6.27-7-generic              2.6.27-7.14                       
    Linux kernel image for version 2.6.27 on x86
ii  linux-image-generic                       2.6.27.7.11                       
    Generic Linux kernel image

Reinstalling linux-image-2.6.27-7-generic will get the proper entry
added into the grub menu.

-- 
Installing into an existing / partition will result in a broken kernel
https://bugs.launchpad.net/bugs/287747
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