E-mail Stuck in Outlook Outbox

A client just called me, and they had three messages stuck in their Outbox in Outlook 2010 on a Windows 7 machine (though these instructions apply to other versions of Outlook and Windows as well). The messages had unusually large attachments, and Outlook could never send them before timing out (or getting stuck, not sure exactly what was holding them up). When I checked the Send/Receive Progress screen, it showed that the messages were being sent and had no errors listed. Here’s what I did to solve the issue:

  1. Clicked on the Send/Receive tab, and then clicked “Work Offline”.
  2. Closed Outlook completely.
  3. Open up Task Manager (you can usually do this by pressing control + alt + delete and then choosing “Open Task Manager”). Click on the “Processes” tab and make sure that Outlook.exe is not present in the list. If it is, click on it and press delete to close it down completely.
  4. Reopen Outlook. It should have remained in offline mode (you can verify this on the status bar at the bottom of the window or by clicking on the Send/Receive tab and seeing if “Work Offline” is still highlighted.
  5. Go to the Outbox, and you should now be able to delete the messages (if you just want to get rid of them altogether). Otherwise, if you want to modify the messages instead of deleting them, you can drag them into the Drafts folder and then edit them before attempting to send them again.
  6. When you are finished deleting or modifying the messages, remember to go back to the Send/Receive tab and click “Work Offline” again to deselect it, allowing Outlook to go back online.

After following these steps, we were able to delete the first message that was getting stuck and modify the second so that it would send. We thought the third message would send once the second one did, but it didn’t. We had to repeat the steps listed above to move the third message into the Drafts folder. After putting Outlook back online, we went into the Drafts folder, opened the message, and then clicked “Send”. The third message was finally sent successfully.

6 thoughts on “E-mail Stuck in Outlook Outbox

  1. garden bay

    I have just changed my laptop, and all my e-mails are lying on Outlook Express which I was using on my old laptop. I am really stuck right now because I cannot figure out a way to transfer the e-mails to my new Outlook 2007. I had copied the files as dbx files but realised there is no way to copy them. Please help me. Thanks,

    Reply
  2. Garden Bay

    My mom is using OE version 6 in WIN XP.
    She is able to get mail but whenever she tries to send mail it gets stuck in the OUTBOX.
    The mail is sent but still jams the outbox & if not deleted it is sent over & over again.
    How can I fix this? What is an alternative for OE 6? Thanks … -A

    Additional Details
    ** Note there is no mistake in Email setting..mail is being sent but still is stuck in Outbox. Also, it doesn’t appear in Sent box. I don’t wish to change to another mail format but stay with OE format. -A

    Reply
    1. Beth Post author

      There is a setting in OE where you can specify where copies of outgoing messages should be saved. Usually, this is a “Sent” folder, but sometimes, this gets reset to the Outbox, so then every time you send a message, it saves a copy of it in the Outbox, which then in turn, sends it again. That could be what is causing your issue (especially since you said that messages are not being saved to the “Sent” folder.

      For alternatives to OE, I’d take a look at Thunderbird. It’s free, and I find it easier to use than OE. Additionally, OE is no longer being supported since they dropped OE as a separate software package after Windows XP. You can get Thunderbird for free from Mozilla: http://www.mozilla.org/en-US/thunderbird/.

      Reply
  3. Kelly

    Thanks for the help. I had found similar solutions … but none worked.

    The step most were missing was

    “Open up Task Manager (you can usually do this by pressing control + alt + delete and then choosing “Open Task Manager”). Click on the “Processes” tab and make sure that Outlook.exe is not present in the list. If it is, click on it and press delete to close it down completely.”

    Reply
  4. Arnie Lakeyn

    I kept getting a message that an email was sending when there were no emails in my Outbox. I kept getting the pop up message and it was non-stop. I restored my computer to an earlier date and it went away.

    Reply

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