I think I have experienced this problem upgrading from 'hardy' to
'intrepid'.

It seems that the grub update step isn't synchronised with the
installation of the new kernel, and the generation of a new initramfs.
In my case, I ended up with a menu.lst that listed the new kernel, but
did not have a corresponding initrd line for it. The menu.lst was
generated at a time when the kernel image was there, but the initramfs
had not yet been created. The new kernel would not boot. Fortunately an
old one would.

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menu.lst not updated after kernel update
https://bugs.launchpad.net/bugs/290140
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