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Outlook duplicating past messages

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I've read through the forums and haven't seen a thread addressing my issue. My apologies if I'm wrong.

So we have Office:mac 2011 and we're using Outlook for my boss' e-mails. He had issues where the program would resync old messages- thousands at a time, but we did a fresh install and everything works out well. He doesn't mess with ANY settings and out of the blue Outlook downloads and syncs about 100 messages, at random. Random dates, random times, random contacts and subjects. I've had 0, absolutely, 0 issues with yahoo mail using thunderbird.

Can anyone help in finding cause to this? All his settings are fine, he can send and receive, and it happens literally at random. At times he's not even on the computer when it does so.

Thanks

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