Is your Outlook sending the same email multiple times? Usually happening when you are trying to send large attachments? There are a couple of possible reasons:

1. The most likely cause is that you have your Send/Receive timer set too low. For example if your Send/Receive timer is set to 1 minute, if the email takes longer than a minute to send, it will still be sitting in the outbox when the next Send/Receive is run - causing it to try sending again. 
2. If that's not the case, it could be that your Sent Items folder is full. Outlook does some funny things when it's full so try archiving them to see if that solves the issue.
3. Failing that, try to do an Office Repair.

Tried the above? Has it worked for you? Let us know!

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