Fixing Outlook's problem where emails with large attachments stay in the outbox yet the message sends multiple times to the receipient

Outlook as a common problem sending emails with large attachments over 1 or 2 MB. These emails might stay in the outbox and appear to take forever to send but recipients actually receive the email (and attachment) over and over (sometimes 50 times or more). The problem may lie with the server timeout setting in Outlook.

Outlook waits a default time of 1 minute before timing out. The next time it checks for mail, which by default is automatic (not requiring a click of the 'Send/Receive' button), the message will still be in the queue and it will resend it. Extending this timeout setting in Outlook has been known to remedy this problem.

Go to Tools > E-Mail Accounts > View or Change Existing Accounts > Click Next. Select the email account that is problematic and click Change > More Settings > Advanced. On this screen, increase the Server Timeouts value. Try a setting somewhere between 3 and 5 minutes depending on the size of your attachments. Click OK > Next > Finish.

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