This is the state of my boot partition immediately after the upgrade
failed:

#df /boot
Filesystem     1K-blocks      Used Available Use% Mounted on
/dev/sda1         163322    152984      1906  99% /boot

I had removed a kernel package just before the update, because this
issue has affected me in the past. When I began do-release-upgrade the
Use% for /boot was 68%, i.e. I had 52263 IK-blocks (51 MiB) free.

For comparison, 
# du -BK /boot/*3.5.0-27*
shows that the four packages  linux-headers-3.5.0-27, 
linux-headers-3.5.0-27-generic, linux-image-3.5.0-27-generic, and 
linux-image-extra-3.5.0-27-generic (my currently running kernel) consumes 37.63 
MiB on /boot, so I thought I was safe.  Go figure...

My fix: since this is an upgrade, remove the *oldest* kernel package set 
installed, which in my case was 3.5.0-17.
# dpkg -l | grep 3.5.0-17 | cut -b5-45 | xargs apt-get -s -y purge
The following packages will be REMOVED
  linux-headers-3.5.0-17* linux-headers-3.5.0-17-generic* 
linux-image-3.5.0-17-generic*  linux-image-extra-3.5.0-17-generic*

** The above command includes the -s 'simulate' switch.  When you're
happy with what will happen, repeat it without the -s **

I did, and apt-get proceeded to configure the new kernel (3.8.0.-19.35).
Now /boot has 32944 available blocks.

The conclusion seems to be that the kernel package installation uses
much more space while working than when it has finished; 51 MiB free is
insufficient to install a package set which uses less than 39 MiB of
/boot.

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https://bugs.launchpad.net/bugs/1173468

Title:
  kernel-image package doesn't check free space on /boot

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