Apparently this was fixed in Karmic starting with dhcp3 3.1.2-1.
Quote from the changelog:
* debian/rfc3442-classless-routes: also run for REBOOT reason (closes:
#515756)
http://bugs.debian.org/cgi-bin/bugreport.cgi?bug=515756
** Bug watch added: Debian Bug tracker #515756
http://bugs.debian.org/cgi-bin/bugreport.cgi?bug=515756
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[jaunty] option rfc3442-classless-static-routes causes missing routes
https://bugs.launchpad.net/bugs/307204
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