A new version of the Calendar Printing Assistant has been released which adds support for Outlook 2010.
To install this new version, you must first uninstall any previous version of the Calendar Printing Assistant from your system.
Sadly, nothing seems to have changed and even the application installer and the application itself are reporting still that it is meant for Outlook 2007. It does work with Outlook 2010 now though, so it really appears that they only added support for Outlook 2010 and changed nothing else in the application.
Download: Calendar Printing Assistant 2.0