Here is what is causing the error:

Setting up grub (0.97-29ubuntu36) ...
dpkg: error processing grub (--configure):
 subprocess post-installation script returned error exit status 3
...
Setting up linux-image-2.6.27-4-generic (2.6.27-4.6) ...
Running depmod.
update-initramfs: Generating /boot/initrd.img-2.6.27-4-generic
cp: cannot stat `/etc/udev/rules.d/85-lvm2.rules': No such file or directory
Running postinst hook script /sbin/update-grub.
Searching for GRUB installation directory ... found: /boot/grub
Searching for default file ... found: /boot/grub/default
Testing for an existing GRUB menu.lst file ... found: /boot/grub/menu.lst
Searching for splash image ... none found, skipping ...
Found kernel: /boot/vmlinuz-2.6.27-4-generic
Found kernel: /boot/last-good-boot/vmlinuz
Found kernel: /boot/vmlinuz-2.6.24-21-generic
Found kernel: /boot/vmlinuz-2.6.24-17-generic
Found kernel: /boot/memtest86+.bin
Merging changes into the new version
 Conflicts found! Please edit `/var/run/grub/menu.lst' and sort them out 
manually.
 The file `/var/run/grub/menu.lst.ucf-new' has a record of the failed merge of 
the configuration file.
User postinst hook script [/sbin/update-grub] exited with value 3
dpkg: error processing linux-image-2.6.27-4-generic (--configure):
 subprocess post-installation script returned error exit status 3

I reassign. Could you please attach your /boot/grub/menu.lst ?

** Changed in: update-manager (Ubuntu)
   Importance: Undecided => Medium
       Status: New => Triaged

** Changed in: grub (Ubuntu)
Sourcepackagename: update-manager => grub

-- 
package update-manager 1:0.93.19 failed to install/upgrade: ErrorMessage: 
SystemError in cache.commit(): E:Sub-process /usr/bin/dpkg returned an error 
code (1)
https://bugs.launchpad.net/bugs/277642
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