Error -19761 when sending mail (The send or update operation could not be performed because the change key passed...)

Anonymous
2016-10-04T16:13:47+00:00

I’m having a problem with one user in our system. Details are as follows:

Platform: OS X 10.10.5

Outlook version: Outlook for Mac 2016 (15.26.1)

Problem: Randomly (about 5-10 times through the work day), when the user sends an email, they get an error in Outlook for Mac, the message is not sent, and the message is put in their Drafts mailbox. The error that is displays is as follows:

The send or update operation could not be performed because the change key passed in the request does not match the current change key for the item., Cannot submit message.SaveStatus: IrresolvableConflict

PropertyConflicts: Mail could not be sent. The message has been moved to your Drafts folder.

Account name: "XXX"

Error: -19761

They then open the message from their Drafts folder and attempt to resend it. It then sends without issue.

Some additional notes:

  • The error started happening 2 days ago—no changes were made to the user’s machine prior to the error appearing.
  • The error happens when sending to both internal and external contacts.
  • The error only happens when using Outlook for Mac desktop client (the issue does not happen when sending mail via OWA or iPhone, etc.)
  • We have updated Outlook for Mac to the latest available version (15.26.1).
  • We have deleted/re-added the account in Outlook.
  • We have uninstalled/reinstalled the Office 2016 package on the computer.

Any advice would be appreciated.

Thanks,

Kristin.

Outlook | MacOS | Legacy Outlook for Mac | For business

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  1. Anonymous
    2017-02-06T20:15:46+00:00

    Alright folks - I think we were finally able to identify the race condition that was causing this mess.  As of build 15.01.0917.000, you should no longer be hitting this issue.  Note that in an EWS response, the SOAP header indicates what build you are on.  Sorry this one took so long.

    The basic issue was that even though you were doing a "new" operation, there are these various processors on the server side that were touching the item, and one or more of them were touching and saving the item as part of their processing.  As such, the item "looked" different and the store would complain that the change key was stale.  The fix was to ensure that no "saves within saves" occurred.

    Just to reiterate, there is nothing wrong with your client or client cache - this was a server side only condition and the only workaround was to send the item from the draft folder (which is obviously not an acceptable solution).

    Also note that this is not specific to EWS - it will also affect the REST API and really any protocol that Exchange offers.

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  2. Anonymous
    2016-12-16T18:40:50+00:00

    That was one of the suggested troubleshooting fixes suggested by MS for us, but didn't work. Problem just returned again a few days later. Still waiting on a fix...

    k.

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  3. Anonymous
    2016-12-16T17:10:09+00:00

    I was able to resolve this issue.

    Envrionment: Mac OS upgraded in place to Yosemite, and Office 2016 for Mac installed on top of Office 2011 install. Using Office 365/Exchange Online.

    I had the same issue described where user would send message and get a sync error, and message went to drafts folder.  Another symptom I noticed was that when adding a new account in Outlook, autodiscover was not detecting outlook.office365.com and I had to enter that manually. Other users logged in to the same Mac did not experience this problem leading me to believe it was an issue with the profile/identity.

    Resolution: rebuild Outlook profile (used to be called Identity in 2011).

    Steps:

    • Quit Outlook
    • In Finder, browse to the Application folder.
    • Right click Outlook app, Show Package Contents.
    • In the Contents > SharedSupport folder, open Outlook Profile Manager (previously called Database Utility).
    • In the Outlook Profile Manager window, click the Remove (-) button to remove the default profile.
    • Close profile manager
    • Relaunch Outlook
    • Configure new profile

    After making this change emails send 100% with no problems.

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  4. Anonymous
    2016-12-09T19:24:04+00:00

    Hi Guys, i'm having the exact same issue/error. 

    "change key passed in the request does not match the current change key for the item"

    Started happening about a week ago. I think right after Office update 14.7.0 was installed. 

    Has happened about 20 times randomly. Never same contact and mostly on replies. When i got to drafts, i can try to send again and most times it will send correctly on 2nd try. 

    I use office 365 with host Godaddy. they say issue is Microsoft/Outlook. i only use Outlook interface for sending/receiving.

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