We've had this in the past, the user will send multiple attachments in a single message. When received (and in their sent items), when you open Document A, it will actually be Document B. Document B will actually be Document C, etc... In the past, we had a local metadata cleaner running on the pc's, Workshare, so we blamed the issue on that. It seemed to happen less than a handful of times in one year in our firm. Now, we no longer have a local metadata scrubber, it is server based. When a user sent 30 attachments in a single message (yes, I know) to both an external and internal person, the filenames were swapped on the attachments as above for even the INTERNAL person. Since the message to the internal person never goes through the metadata cleaning server, we now know that is not the cause. Instead, the blame must lie either with Outlook 2010 or Exchange.

In my research, I've found reports of this happening in the past with Outlook 2003 (we had it then occasionally too), no real, true answers, but to keep the Outlook Secure Temp folder cleaned out. So, now I ask you, have you had this happen in your organization before? Any answers on how/why?