Hello. My name is***** can help you with your question.
The Calendar Printing Assistant for Outlook is designed to work with Office 2007, and there are bugs when trying to use it under Office 2010. The last update to the printing assistant was in 2010. Is there any pattern to what appears to be missing? If it is something other than a bug, I'll help you figure out what it is if I can. So to answer your question - there is no known solution for this, but that won't necessarily stop of from solving it.