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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”

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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:

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

image

 

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:

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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:

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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

  • Anonymous
    January 01, 2003
    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!!!

    • Anonymous
      September 29, 2016
      I looked in my Com Add-Ins, and iCloud was not listed.
      • Anonymous
        September 29, 2016
        So where do I go from here? Should I remove iCloud, or perhaps re-boot to a previous date? If I did that, would it clear out these iCloud issues?
      • Anonymous
        January 26, 2017
        I agree, I went in and iCloud was not listed. I disabled all of the ones listed ??

  • Anonymous
    January 05, 2013
    Thanks, had same problem, this was a lifesaver

  • Anonymous
    January 08, 2013
    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.

    • Anonymous
      January 05, 2017
      yes, i found this "workaround" to work as well...i need to icloud add-in to be active as I want my icloud calendar to sync with Outlook calendar which only works with the icloud add-in. Such a pain though.

  • Anonymous
    February 27, 2013
    Same problem in Outlook 2010.  Worked like a charm-  Thanks!

  • Anonymous
    March 31, 2013
    Same problem with Outlook 2013. This was the solution! excellent!! tks!

  • Anonymous
    April 22, 2013
    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.

  • Anonymous
    May 07, 2013
    Many thanks! This has been haunting me for months!

  • Anonymous
    May 21, 2013
    The comment has been removed

  • Anonymous
    June 04, 2013
    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! :)

  • Anonymous
    July 23, 2013
    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!!!

  • Anonymous
    September 14, 2013
    Awesome.  Thank you so much for posting.

  • Anonymous
    October 04, 2013
    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.

  • Anonymous
    October 25, 2013
    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

  • Anonymous
    November 19, 2013
    Thank you so much. My problem was the Norton anti spa add-in. removed problem solved.

  • Anonymous
    November 21, 2013
    Thank you SteveC -- that works for me

  • Anonymous
    December 03, 2013
    Same issue here, at this time looks like Symantec EndPoint addon issue.

  • Anonymous
    January 22, 2014
    The comment has been removed

  • Anonymous
    February 08, 2014
    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).

  • Anonymous
    June 09, 2014
    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.

  • Anonymous
    August 28, 2014
    The comment has been removed

  • Anonymous
    November 06, 2014
    @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.

  • Anonymous
    November 17, 2014
    My role has previously primarily focused on Microsoft Intune, nowadays it’s more towards our whole Enterprise

  • Anonymous
    February 11, 2015
    Worked a treat. Thank you for posting.

  • Anonymous
    April 18, 2015
    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.

  • Anonymous
    August 04, 2015
    Same problem, different plugin for me, this was a lifesaver, thanks!

  • Anonymous
    October 12, 2015
    Thanks, SteveC. All these years later and your workaround worked for me, too.

  • Anonymous
    December 26, 2015
    Godsend. Thank you so much!

  • Anonymous
    June 07, 2016
    The comment has been removed

  • Anonymous
    June 22, 2016
    If we are still having this issue but do not have the iCloud plug-in, what do you recommend?

    • Anonymous
      October 03, 2016
      Outlook 2013: File tab, Options, Add-ins.Click Go button at the bottom of the dialog to disable add-ins. Select Disabled Add-ins from the drop down menu.

  • Anonymous
    September 29, 2016
    I foolishly installed iCloud on my iphone and it , by it's own volition, set itself up on my PC. Now I am having difficulty with Outlook in that when I create an email, it frequently, but not always, saves new these emails in the DRAFT mode, but still are located in the OutBox. Can ANYONE help me to resolve this frustrating situation?

    • Anonymous
      September 29, 2016
      I looked in my Com Add-Ins, and iCloud was not listed.Can anyone advise if I should uninstall iCloud and what are the expected negative ramifications for doing that? I have read a lot of horror stories on the net on that very topic.
      • Anonymous
        September 29, 2016
        The comment has been removed
        • Anonymous
          September 29, 2016
          The comment has been removed
          • Anonymous
            October 03, 2016
            YEAH Microsoft fixed the problem, and it was a simple fix. THANK YOU MICROSOFT_____________________________________________________________________________Outlook 2013: File tab, Options, Add-ins.Click the Go button to disable com addinsClick Go button at the bottom of the dialog to disable add-ins. Select Disabled Add-ins from the dropdown menu to re-enable add-ins.
          • Anonymous
            October 03, 2016
            YEAH Microsoft fixed the problem, and it was a simple fix. THANK YOU MICROSOFT_____________________________________________________________________________Outlook 2013: File tab, Options, Add-ins.Click the Go button to disable com addins . Select Disabled Add-ins from the dropdown menu to re-enable add-ins.

  • Anonymous
    November 01, 2016
    Thank you! Mine was a WebEx add in that cause this behavior. After disabling/re-enabling, all worked as before.

  • Anonymous
    December 13, 2016
    The comment has been removed

  • Anonymous
    January 26, 2017
    Based on the above - I'm using ICloud for contacts and calendar - so I assume I need the plugin enabled. How do I resend an email from the outbox after I've edited it? Or do I have to copy it and rebuild the email - a real pain!

  • Anonymous
    February 02, 2017
    Thank youuuuu !!!! :D

  • Anonymous
    May 18, 2017
    Thank you for the hint. I recently found that the WebEx Productivity Tools cause the same issue.The investifgation was easy for me, had only installed two software packages and separately disabled the Outlook add-in of each of it and restarted OL (dono if necessary) and found phenomenon gone after the 2nd one.

  • Anonymous
    August 21, 2017
    Had this problem in Outlook 2007 SP3 \ Outlook 2013. Also i try to find answers with referring lot of online resources.But still couldn't found proper solution for this.Thanks,