I can confirm that upgrading from a fresh wubi install of 10.04.1 to
10.10 currently fails to boot after successful completion, both for
32bit and 64bit installs. Only in the 32bit case do I get a grub prompt
- in the 64bit case, the machine just reboots after selecting ubuntu
from the list of operating systems.

I can also confirm that this behaviour is fairly recent, and that a
previous upgrade from 10.04.1 to 10.10 worked in a 64bit wubi
environment. In that case, an automatic security update of 10.10 made it
impossible to boot.

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Can't boot Ubuntu after an upgrade from 10.04.1 to 10.10
https://bugs.launchpad.net/bugs/653134
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