In case this helps anyone else... After upgrading to Lion, I lost the ability to open attachments from Outlook 2010 in my Windows 7 VM to Acrobat Pro on the Mac. The application focus would move away from Outlook and Acrobat would launch, but the file would not open. Saving the attachment file and then right-clicking on it in Windows Explorer and selecting Open With... Adobe Acrobat Pro (Mac) resulted in nothing happening. Similarly, nothing happened when selecting Open With... Preview (Mac). Right-clicking it and selecting Open on Mac worked fine. The solution was simple enough -- I'd swear I had already updated to the latest Parallels build the other day, but there was a new one. I installed it and manually updated Parallels Tools. Now attachments open fine on the Mac (if a bit slow) from within Outlook.