I have a similar problem, which matches the description above.

df -h /boot
Filesystem            Size Used Avail Use% Mounted on
/host/ubuntu/disks/boot
                       73G   25G   49G  34% /boot
n...@ubuntu:/boot$ 

here i s what happens:

sudo apt-get upgrade
Reading package lists... Done
Building dependency tree       
Reading state information... Done
The following packages will be upgraded:
  linux-image-2.6.27-7-generic
1 upgraded, 0 newly installed, 0 to remove and 0 not upgraded.
Need to get 0B/23.4MB of archives.
After this operation, 0B of additional disk space will be used.
Do you want to continue [Y/n]? 
(Reading database ... 128835 files and directories currently installed.)
Preparing to replace linux-image-2.6.27-7-generic 2.6.27-7.14 (using 
.../linux-image-2.6.27-7-generic_2.6.27-7.16_i386.deb) ...
Done.
Unpacking replacement linux-image-2.6.27-7-generic ...
dpkg: error processing 
/var/cache/apt/archives/linux-image-2.6.27-7-generic_2.6.27-7.16_i386.deb 
(--unpack):
 unable to make backup link of `./boot/vmlinuz-2.6.27-7-generic' before 
installing new version: Operation not permitted
dpkg-deb: subprocess paste killed by signal (Broken pipe)
Running postrm 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-2.6.27-9-generic
Found kernel: /boot/vmlinuz-2.6.27-7-generic
Found kernel: /boot/vmlinuz-2.6.27-3-rt
Found kernel: /boot/memtest86+.bin
Updating /boot/grub/menu.lst ... done

Errors were encountered while processing:
 /var/cache/apt/archives/linux-image-2.6.27-7-generic_2.6.27-7.16_i386.deb
E: Sub-process /usr/bin/dpkg returned an error code (1)

-- 
i have been consitently unable to install "linux-image-2.6.27-7-generic"
https://bugs.launchpad.net/bugs/302113
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