Outlook - Message Won’t Send, Stuck In Outbox
March 10th, 2008Problem
Once a message goes into your outbox, Outlook tries to send it. While it’s trying, there’s little you can do. If you try to delete it, move it or even open it you will get an error message that says Outlook is sending the message.
The problem is trying to send an email larger than your Internet Service Provider (ISP) will allow. ISP’s put a limit on the size for a single email that it will accept. Currently it varies depending on your provider. Comcast indicates a 10MB limit while AOL lists a 16MB limit and some ISP’s may be as high as 50MB.
When an email gets rejected by the ISP because it exceeds the limit, it returns an error that Outlook doesn’t interpret as a fatal error. Outlook then tries to resend the message. This loop will continue until the message is removed from the outbox, either deleted or moved to a different folder. But this con not be done while Outlook is stuck in the loop of trying to send the email.
Solutions
Two techniques to stop Outlook from continually trying to send the oversized email.
- Use Outlook in offline mode. To change Outlook to offline, click File, then click Work Offline. This should put a check next to Work Offline and put Outlook in offline mode. Now you should be able to delete or move the email out of the outbox where it can be dealt with. This method does not work 100%. If you still are unable to work with the email use the next method.
- Froce Outlook offline. Disconnect your internet/network cable from the back of your computer or router if your using a router. It looks like a phone jack but a little larger. Or you may be connected via USB. In which case unplug the USB cable that connects your computer to the internet. Once the computer recognizes the the connection is lost, you will be able to work with the oversized email.
Options for sending large files
- I recommend Skydrive. Free from Microsoft as part of their Windows Live services.
- 5 GB of free online storage, available from any computer with Internet access.
- Create personal, shared, and public folders — you decide who has access to each folder.
- Windows Live SkyDrive works well on any Windows or Macintosh computer with Firefox 1.5 or higher, or Internet Explorer 6 or higher.
- Most instant messengers also have a built in file transfer, but both parties need to have the same or compatible messengers. I recommend Skype here. It not only has an unlimited file transfer size, but it’s also a Great phone, chat and communications tool.
- Another option is to upload the file to a free file hosting service like RapidShare. I’m not a big fan of these. They may be slow, have file restrictions or other barriers.
- My Last option is to split the file into smaller pieces and compress it. Then send each smaller peice in an email. For this I suggest 7-Zip. A free open source project.

