Running through this process myself I discovered the following in my
boot partition at the time of the failure:

16M initrd.img-3.8.0-19-generic
16M initrd.img-3.8.0-19-generic.dpkg-bak
   0M initrd.img-3.8.0-19-generic.new

So it seems that the new kernel image is getting created multiple times
during the upgrade process.

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

Title:
  release upgrade doesn't properly calculate free space needed for /boot

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