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A few users testing our Citrix XenApp service found that several (seemingly random) previously sent emails were sent out immediately after they logged into Outlook via Citrix for the first time.

The problem hasn't occurred for them since. After one user had this happen, and we scratched our heads about it thinking it was a fluke, our IT director had this same issue. I guess I'd rule out any PEBKAC issues.

I really don't know where to begin troubleshooting this problem. If you have any ideas what could have caused this, I'd appreciate you sharing them, as strange or far-fetched as they may seem :)

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What do you mean "old emails"? Emails that have already been sent and are in the Sent Items folder? Is Outlook configured in MAPI mode or POP mode?

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Yes, by old emails I mean a set (a few dozen) of previously sent emails were sent out. It is seemingly random. We have Outlook connected to Exchange using cached mode. – Ken Pespisa Feb 19 '10 at 14:41
If you can reproduce the problem at will (probably not) or if you have a particular user that seems to be affected, try disabling cached mode for that individual and see if it helps. There may be some kind of disconnect between the ost file and the mailbox. – joeqwerty Feb 20 '10 at 0:24

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