Help – I tried to send a giant attachment and it’s stuck in the Outbox!

“I tried to send a large attachment to a friend and now the e-mail is stuck in my Outbox! I’ve been trying to delete it and I can’t because Outlook says it’s still trying to send it. Help!”

This is a fairly common issue that we’ve heard a lot of users report through the blog, so we wanted to write a quick post and explain the easiest way to get out of this situation.

E-mail messages can get stuck in the Outbox for a few different reasons, but the most common case happens when the e-mails are very large (megabyte-wise) due to their attachments. You may even see errors like “Outlook is transmitting the message” when trying to delete them from the Outbox.

So if you’ve got an e-mail stuck in your Outbox and you can’t re-open it, try this:

  1. Go the File menu, then choose Work Offline in order to stop Outlook from trying to send all mails:


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  2. Switch to the Outbox.
  3. You now have two options:

    a. Move the message: you can drag-and-drop or use the Edit: Move to Folder menu item to move the e-mail to your drafts folder. This will allow you to re-open the offending e-mail and slim it down by removing the large attachments before attempting to resend it.

    b. Delete the message: this will immediately remove the message from the Outbox and put it in Deleted Items.

  4. If you receive an error at this point that says the message is being transmitted, close Outlook, wait for Outlook to exit (you may need to use Task Manager and wait for the Outlook.exe process to exit), and then start Outlook again and repeat steps 2-3. In some cases, the item may not be released until Outlook has restarted.

  5. Go to the File menu, deselect Work Offline to start sending and receiving mail again.

Instead of sending a large attachment, consider putting the file on a local network share or a SharePoint site inside your company and then sending a link around:

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For details on how to add a link, see: Use hyperlinks in Outlook items and/or Add links containing spaces to an e-mail message.

If you’re sending it to users outside your company or are just sharing files with friends, you can use Windows Live SkyDrive as a cool and convenient way to store and send large files around.

Hope that helps get you unstuck!

Updated 7/31: Added a new step 4 to restart Outlook if you receive an error that the item cannot be moved or deleted. Based on comments from readers of the blog, under some circumstances working offline may not be enough to let you move the item. If you restart Outlook after selecting Work Offline, Outlook will come back up in offline mode, and should allow you to delete/move the item at that time.

Michael Affronti
Outlook Program Manager

More info on Outlook email attachments:

Email stuck in the outbox in Outlook 2010

Office Blogs Comments

Comments: (88) Collapse

  • That did not help. Outlook replys "Outlook has already started sending message". I am not able to touch the message in any way.

  • This method works but one step has been left out. After selecting File->Work Offline, you must completely close Outlook (use task manager to ensure that it is closed) and then reopen Outlook. You can then delete the errant email or open it and remove the attachment. Be sure to uncheck File->Work Offline when done.

  • I have had a similar problem also, and what i found was that my virus checker was causing the problem. When i deselected from my virus application to check out going emails for viruses, the outgoing large email had no problem when sending it. I do use a pop server service, and it has a limit on size also, as long as i stay under that size, my large emails sizes go through without any problem, as before i used to have issues even with large emails.

  • I'm still having issues after trying the advice above.... I use access my Yahoo email through Outlook and I have one message in my Outbox with a huge attachment. I tried switching to off line mode and deleting or moving it but it doesn't go anyway. I even restarted my computer and re-opened Outlook. Even when I'm in offline mode it says the send/receive status is 25%. So it acts like it's still trying to send it. Will it eventually go through if I just wait or what should I do? Thanks!

  • I am having the same problem, mine has been stuck in the outbox for a week. It is affecting the speed of everything online too. I've tried all of the above suggestions and nothing is getting rid of it.

  • Some of the time, even though the message is stuck in the outbox, my recipiants report they have received the email numerous times. It appears that the mail is continiously being sent until I get it deleted.

  • I did this:

    This method works but one step has been left out. After selecting File->Work Offline, you must completely close Outlook (use task manager to ensure that it is closed) and then reopen Outlook. You can then delete the errant email or open it and remove the attachment. Be sure to uncheck File->Work Offline when done. Now I can't open Outlook. Help!

  • Thanks very much - I dragged and dropped the email into the delete box and now I can send emails again.

  • Hi, I have a friend that has an outlook issue. There is a group of people that consistently receive emails from him, over and over again - and he doesn't send them anything. It's the same people (roughly 15 people or so) - what type of problem could this be? How can we troubleshoot?

  • HELP! I'm having the opposite problem - I was sent a large attachment (family photos) and it keeps trying to receive - over and over and over. I can't stop it. It's preventing e-mails I've received AFTER this one was sent from being uploaded. I have 25 e-mails waiting in line but this one won't load and get out of the way. HELP!

  • Nothig is working, if I try and move the item I am told, (Can't move the item) If I try and delete it it askes me to (The message interface has returned an unknow error, if the problem persists please restart outlook)

  • Once an attachment hits 2 MB, they get stuck in the Outbox, appear not to send, and sometimes keep other email from sending. I've used all the tricks outlined already to delete from the Outbox with success. However, what I really want to do is successfully send email attachments from Outlook 2007 without essentially spamming the recipient without knowing it. I need the email to send, leave the Outbox and go to the Sent Folder like it's supposed to (and did easily in prior versions). This is an application being used by how many corporations and we're going backwards in productivity? Why isn't this issue being fixed? This is one of the many reasons I found myself wandering into a MAC Store the other day.....this and Vista, of course. You're slowing me down MS!

  • Erin: The issue with e-mails with large attachments getting stuck in the Outbox is not an Outlook bug. Outlook is capable of sending large e-mails just as well as small ones. The issue here is that your e-mail provider or ISP has decided to block the capability of sending e-mails over a certain size. When the server tells us that it can't continue a message, Outlook disconnects and then tries again later.

    Switching to another e-mail client wouldn't let you send larger e-mails, although switching your e-mail provider might.

    For e-mails with large attachments, you should consider a different way to send the file, perhaps through FTP, SharePoint, or another website that allows you to upload large files. E-mail is unfortunately not a medium well suited to sending large attachments.

  • I've checked all three of my ISP's and supposedly they are all 10MB+, but I will check again. Thank you for the response.

  • I tried all of these suggestions with no luck. I rebooted and still had the message stuck in the outbox. I hadn't hit send/receive all, because I was afraid that would make things worse, but in desperation did it and was able to cancel it from that box and then delete it permanently. So, the sequence that worked for me was: go offline, reboot, send/receive, cancel, delete. What a relief!

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