In some cases, especially when you have a slow connection to your mail host, extending the mail server time-out may solve it as well. This often happens when you are using a virus scanner that integrates with Outlook or when your Send/Receive interval is set to a very short time. How can I solve this and make sure Outlook only sends out one copy again? It will send it 20-30 times but keeps the email in my Outbox saying that it hasn't been sent (although sometimes it says it's been sent but stays in the Outbox). It doesn't happen with every email with attachments, just occasionally. I'm having a problem with Outlook sending multiple copies of some emails - usually those with attachments.
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