Outlook: Mail stuck after editing in Outbox

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.

Comments (29)

  1. Anonymous says:

    Very nice – same problem here, hard to describe to my tech folks but they found this article, disabed iCloud Plug-In and mail sends fine now after editing a note and resending. Thanks!!!

  2. David says:

    Thanks, had same problem, this was a lifesaver

  3. Steve C says:


    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.

  4. stephen says:

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

  5. MdC says:

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

  6. Grahame says:

    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.

  7. Al says:

    Many thanks! This has been haunting me for months!

  8. Jeff25 says:

    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!

  9. MG says:

    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! 🙂

  10. BLM Ontario says:

    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!!!

  11. brad says:

    Awesome.  Thank you so much for posting.

  12. Ken says:

    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.

  13. Jools says:

    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

  14. Ady J says:

    Thank you so much.

    My problem was the Norton anti spa add-in.

    removed problem solved.

  15. BOBL says:

    Thank you SteveC — that works for me

  16. Trevor says:

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

  17. alana says:

    Thank you so much. This was driving me crazy!

  18. BMWAustin says:

    I tried everything, disable this enable that, create new group, move to draft. Nothing works, there is no pattern just happens randomly (seems to me).

  19. karen says:

    Well, I have this same issue, I think….only I don’t have that plug-in enabled to begin with. Don’t even see it as an option as a matter of fact. I keep deleting these drafts and they keep returning. I don’t see the icon you folks are referencing. It
    has a draft icon in the drafts folder. I delete them and they return a while later.

  20. LJ says:

    Thank you so much for posting this solution. I had the same issue albeit with different add ins. I do not have the icloud add in. The two add ins which were creating the problem were Öpen Text Rightfax Outlook Add-in"and Unified Messaging for Microsoft
    Exchange Outlook Add-In". I disabled both and now my mails (with delayed sending) do not go into draft mode after editing. Thanks again and God Bless.

  21. Jim H says:

    @Steve C, thanks. I am new to outlook and we are using the cloud, so disabling it was not the answer. Your answer worked like a charm.

  22. Anonymous says:

    My role has previously primarily focused on Microsoft Intune, nowadays it’s more towards our whole Enterprise

  23. MT says:

    Worked a treat. Thank you for posting.

  24. Kevin S says:

    I too am using icloud and want to keep syncing my ipad with Outlook. I found that even if you highlight a message that is in the outbox, it will turn it to a draft. to fix the ones that show the draft icon, right click and forward the message. The new
    message is created in the outbox, so go back and right click on the draft message and delete the draft. Now be careful and do not highlight any of the waiting to be sent messages or you will have to do it all over again. To prevent that, highlight the date
    bar above the messages so that no messages are accidentally highlighted.
    This procedure works very well.

  25. mike says:

    Same problem, different plugin for me, this was a lifesaver, thanks!

  26. Rob says:

    Thanks, SteveC. All these years later and your workaround worked for me, too.

  27. nennycakes says:

    Godsend. Thank you so much!

  28. Geoffrey says:

    I had the same issue but for a specific reason. For some years now I’ve always set up a rule which delays an email leaving my Out box for 60 seconds (I’d choose 30 if it was available). This has been a life saver when forgetting an attachment or accidentally sending a confidential item to an inappropriate recipient.
    Then suddenly, & intermittently, I started to get this issue so thank you for the tip. I’m off to try it.

  29. Robert says:

    If we are still having this issue but do not have the iCloud plug-in, what do you recommend?