It isn't the kernel update that broke anything, it's grub2 losing the
ability to see the new kernel file.  In all my tests (I've been able to
reproduce every single error everyone has gotten), grub2 was always the
root cause.

As a test, I created a complete duplicate of my Wubi install as ext3
instead of ext4 root.disk.  Grub2 suffers from the same problem of being
able to read some files fine, others as garbage, and some not at all
(freezing).  I can't say if the problem is being triggered by the
filesystem being on a loopback device, or if grub2 is perhaps having
serious problems seeking into extremely large disk partitions (or a
combination of the two), since /boot isn't a separate filesystem in
Wubi.

Currently I was able to restore my install by creating a simple 200MB
ext2 "boot.disk" as a separate loopback device mounted as /boot, and
keeping the original root.disk as ext4.  I made a very small change to
/usr/share/lupin-support/grub-mkimage so that grub-install writes a
correct wubildr to /host (C:\)pointing to the new boot.disk, as well as
adding a "/boot" entry to /etc/fstab.

So far my system has been running just fine, including having compiled
and installed a custom kernel and initrd to my new /boot filesystem.

At some point I intend to test having /boot as ext3 or ext4.

What I can include from all this is that something is seriously BROKEN
with grub2, though I personally haven't had the time to investigate this
in the grub2 source.

I recommend the Wubi maintainers perform similar tests as I've outlined
above, i.e. small, separate /boot filesystem on it's own loopback-
mounted file, as it's a successful workaround until grub2 gets fixed.

-- 
After 9.10 grub update can not boot into Wubi install
https://bugs.launchpad.net/bugs/477104
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