Converting Outlook 2007 email to PDF; Have to reboot PC to convert multiple times

I have an end user who converts multiple emails to PDF for filing purposes. Adobe converts multiple emails in a portfolio style. Email can be seen as in a file at the top and seen seperately ebelow. After 2-3 times Adobe won't convert to portfolio format, won't give error message, but will convert all selected email as one large PDF. Until user reboots machine, portfolios can't be created.  Tried on two different machines same issue. Using Adobe 9 Pro and Outlook 2007.

Is Acrobat updated to 9.5.2?  What SP do you have installed for Office 2007?  What version of Windows (with SP) is running on these computers?

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