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Outlook: Mail stuck after editing in Outbox

Outlook: Mail stuck after editing in Outbox

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Do you have a situation where you can’t send e-mail after editing a “waiting to be sent” e-mail in your outbox? I helped someone with the same situation, read how I troubleshooted and found the solution.


The scenario

This problem occurred in Outlook 2013 but could very well happen in earlier versions. This user disabled the option to “Send immediately when connected”


After composing and sending e-mail, it would be moved to the outbox. The actual sending of the e-mail would only happen when the user initiated a manual “Send and Receive”.

When editing an e-mail which was waiting to be sent (in the outbox) the icon would change from “waiting to sent” to a “draft”:

E-mail waiting to be sent in Outbox:


After editing the e-mail which was located in the outbox, the icon changed to draft:



As soon as you will press “Send” in the edited e-mail, the icon will change again to the little envelope and the e-mail would be sent after manually pressing “Send and Receive”. So far, this is all by design.

In this scenario, after pressing “Send” the e-mail would retain the draft icon and therefore would never leave the building. We found no way of sending an e-mail which was edited in the outbox.

How to troubleshoot

I tested it on a different machine and the behavior was different, an e-mail which was edited in the outbox would be waiting to be sent after hitting “send”.
To test if any plugins are responsible for this behavior we started outlook in safe mode:



When Outlook was running in safe mode, no plugins are loaded and the problem did not occur!

The quickest way to find the responsible plugin is by simply eliminating them, enable a few and restart outlook (not in safe mode) and see if the problem occurs.

After doing a few test I found the responsible plugin:


After disabling the iCloud plugin the problem did not occur.

This user did not use the Outlook functionality of iCloud so disabling was the solution. If the functionality is used, an update or follow-up with the vendor would be necessary.

  • Thanks, had same problem, this was a lifesaver

  • Hi

    There's a workaround that doesn't involve disabling iCloud.

    Move the edited e-mail into drafts (drag it) then open it & hit send; then immediately hit send/receive.

  • Same problem in Outlook 2010.  Worked like a charm-  Thanks!

  • Same problem with Outlook 2013. This was the solution! excellent!! tks!

  • Thank you, I had the same issue with emails marking themselves as draft in my outbox, and disabling the iCloud Add In made everything work correctly.

  • Many thanks! This has been haunting me for months!

  • Had this problem in Outlook 2013 and it was driving me CRAZY!  Firstly, I did not know what the symbol was (i.e. that it was a Draft email in my outbox) - I think there needs to be a glossary of Office images - I could not find any online.

    Next - the plugin option seemed plausible and I was going to try it but Steve C's approach was straight-forward and worked perfectly.

    @Steve C - thumbs up! Thanks!

  • Hi guys, same problem in Outlook 2007.

    An email (only 303 kB, 2 attachments) refused to go out no matter what I did.It was composed yesterday while having Google Sync issues, and working offline.

    Later I even tried moving in to Drafts (both as Working Offline and Online), open it and send it from there - nothing changed. I even deleted it, composed it again - same problem. Other emails composed today flew out without hesitation.

    Then somehow @Steve C's method worked, although I was sure I did it the same way myself. Obviously I didn't.

    I didn't bother finding a potential conflict with the plugin.

    Thank you so much! :)

  • Had this problem occur suddenly after months of using Outlook without difficulty.  I did many searches online and tried a number of other suggestions first. Then finally found your blog.  Disconnected the add-in and problem solved!  You are the only one out of many to correctly identify this problem.  Thanks a bunch!!!

  • Awesome.  Thank you so much for posting.

  • I have been through two online sessions with Microsoft Techs (after paying for the "premium support" because the problem was such a pain) and neither one referenced iCloud. They rebuilt my accounts, and that indirectly disabled the iCloud add in.

    I have to wonder, though, why it took a year or so after I installed Outlook and used iCloud, before one of the Microsoft updates (my guess is that this is the cause) chose to disable the iCloud functionality.

  • Brilliant - thanks.  May have some more questions!  Couldn't find add-ins immediately... want to explain: File - Options - Add-ins - Manage and Go!  ??

    Very many thanks again

  • Thank you so much.

    My problem was the Norton anti spa add-in.

    removed problem solved.

  • Thank you SteveC -- that works for me

  • Same issue here, at this time looks like Symantec EndPoint addon issue.

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