Fresh Ubuntu 9.10 wubi install here.  And here's the deal:
After updating and regenerating /boot/grub/grub.cfg (which is the same as 
original), a fresh boot drops me to the grub prompt.  Grub2 is unable to read 
any text files at all now, which is the obvious reason for being dumped to the 
grub prompt.  "cat /boot/grub/grub.cfg" gives a screen full of garbage.  Even 
"cat /etc/passwd" gives garbage.  "ls" can find the files just fine.  I can 
still boot manually by giving the proper "linux" and "initrd" arguments.  These 
files are NOT ACTUALLY CORRUPTED, they can be read just fine in ubuntu.  Only 
grub can no longer read them.  That's problem #1.

Now, problem #2: if you build a fresh kernel from source and install it
into /boot, grub2 can't boot it.  "Invalid magic number" is the error,
no matter what you do.  I first ran update-grub, which creates the
proper grub.cfg in /boot/grub, but it's unreadable while in grub2 (see
above problem).  The grub.cfg is perfectly readable when booted in
ubuntu.  I also tried running grub-install after, which only modifies
the "wubildr" file in the root directory of my windows drive
("wubildr.mbr" is untouched).  This makes no difference.  Worse still,
if you move, rename, etc., the original stock generic kernel or initrd
from the base install, grub will NEVER LOAD IT AGAIN at boot, you'll get
the same "Invalid magic number" error in grub as you would from building
your own kernel.  I already killed a fresh install this way.  Despite
booting from usb and mounting/chroot my install, running grub-install a
million times couldn't fix that problem.  grub-install also leaves
behind a whole mess of seemingly useless files in /boot/grub.  And yes,
I've verified that I'm running the grub-install wrapper from the lupin
package.

Summary: Moving, renaming, or regenerating ANY file, whether it's the
kernel, initrd or grub.cfg results in those files becoming unreadable by
grub2, probably because they're not being found in the correct place on
the drive, resulting in garbage for text files, and invalid magic
numbers for binaries.  Also, grub-install's modification of C:\wubildr
has no effect, and it also leaves behind a mess in /boot/grub on the
linux side.

I'd say this is pretty serious, since I already rendered my original
install completely unbootable as a result of these problems.

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