The log shows that byte-compiling some files failed:

Setting up checkbox (0.9.2) ...
pycentral: pycentral pkginstall: error byte-compiling files (52)
pycentral pkginstall: error byte-compiling files (52)
dpkg: error processing checkbox (--configure):
 subprocess installed post-installation script returned error exit status 1

This is not a checkbox bug proper, but seems to point to corrupted data.
My suggestion would be to apt-get clean and then reattempt installing
checkbox.

Since this report is somewhat old, is not strictly related to checkbox
(but rather to a possibly transient glitch in the upgrade process) and a
new Ubuntu LTS (12.04) is now available, I'll mark as invalid, but if
you're still running 10.04 and the procedure I suggested didn't work,
please reopen the bug and attach the /var/log/apt/term.log file to see
what may have failed. Thanks!

** Changed in: checkbox (Ubuntu)
       Status: New => Invalid

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https://bugs.launchpad.net/bugs/826392

Title:
  package checkbox 0.9.2 failed to install/upgrade: subprocess installed
  post-installation script returned error exit status 1

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