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When you send an e-mail message with a large attachment, you might experience situations where that message is sent repeatedly to recipients — until you delete the message from your Outlook Outbox. The message never appears in your Sent Items folder.

The problem might be related to the connection time-out to your Internet service provider (ISP) (ISP: A business that provides access to the Internet for such things as electronic mail, chat rooms, or use of the World Wide Web. Some ISPs are multinational, offering access in many locations, while others are limited to a specific region.) e-mail server. If the size of the attachment in the e-mail message is too large, the e-mail message cannot be sent within the time limit. As a result, the message is sent repeatedly. To resolve this issue, use the following options:

Option 1: Increase the server time-out limit

1. On the Tools menu, click E-mail Accounts.
2. Click View or change existing e-mail accounts, and then click Next.
3. In the list, click the e-mail account that you want, and then click Change.
4. Click More Settings, and then click the Advanced tab.
5. To increase the maximum time duration for e-mail server connections, under Server Timeouts, drag the slider control.
6. Click OK.
7. Click Next, and then click Finish.

Option 2: Compress the file you are attaching to the message

Zipping a file creates a compressed version of the file that is considerably smaller than the original file. File types that are reduced the most after zipping are text-oriented file types, such as .txt, .doc, and .xls, and graphics files that use noncompressed file types such as .bmp.

See the See Also section in this article for information about zipping files.