Batch Saving Emails to PDF off Outlook

I am having problems printing email batches to PDF off of Microsoft Outlook.  When I attempt to do so, a window pops up saying I don't have the most up to date flash player.  However, downloading the most up to date flash player does not remedy the problem.  In the end, I only get the first page of the first email of the batch PDF'd.  I have had my IT guy look into the issue and he cannot figure it out.