grub2 does try to get this right, so we'll need to investigate why its
attempts fail in your case. Could you please run the following command:
sudo LET_US_TRY_GRUB_2=true sh -x /usr/lib/grub-legacy/update-grub
update-grub.out 21
... and then attach the resulting update-grub.out file to this
Public bug reported:
Binary package hint: grub2
Installed GRUB2, selected chainloading to verify.
GRUB2 installation on /boot/grub/menu.lst seems to look like:
title Chainload into GRUB 2
uuideca12d78-335f-4448-bb2a-251eef2c407f
kernel /boot/grub/core.img