I just checked hplip.preinst. There is a bug in the conffile removal code.
See http://wiki.debian.org/DpkgConffileHandling how to correctly handle this.
In my specifc case
dpkg-query -W -f='${Conffiles}' hplip | sed -n -e \"\\\\'
/etc/udev/rules.d/56-hpmud_support.rules's/.* //p\"
will yield "obsolete", that's why the md5sum comparison fails and the file is
not removed.
The wiki has appropriate code, that strips "obsolete" and spaces.
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/etc/udev/rules.d/56-hpmud_support.rules not migrated/removed on upgrades
https://bugs.launchpad.net/bugs/506793
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