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
    2016-10-12T00:15:49+00:00

    I have 2 users with this exact issue as well. One on Outlook 2011 and one on Outlook 2016.

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  2. Anonymous
    2016-10-11T21:25:29+00:00

    Kristin, Chris, Steve,

    We need to get more extensive logs to investigate further.  Here are instructions:

    First, turn on your troubleshooting logs. To do this click on "Window" in the title bar, then select Sync Errors. 

    In the Sync Errors window, click on the gear icon in the top right hand corner. 

    Check the "Turn on logging for troubleshooting" check box and click “OK".

    Quit and relaunch Outlook.  On next launch, opt to keep logging on when asked.

    Now use Outlook as you normally would until one of these errors pops up.

    Now find the two log files, zip them (they can be very large) and send them to me.

    Log file 1:

    ULS Log:  ~/Library/Containers/com.microsoft.outlook/Data/Library/Caches/Microsoft/uls/com.microsoft.Outlook/Logs

    Log file 2:

    ~/Library/Containers/com.microsoft.outlook/Data/Library/Logs/ folder with the filename "Microsoft outlook-<date>-<time>.log" (a new one will be created every time you launch Outlook and leave logging on.

    (From Finder, hold down Option while clicking on the “Go” menu, then select “Library”)

    Turn off logging.

    I will send you a private message so you can attach the zipped logs to your reply (click on the "Messages" link at top right of the forum page).

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  3. Anonymous
    2016-10-11T16:19:46+00:00

    Yep. Window > Sync Errors displays what I included in the original posting.

    Thanks,

    Kristin.

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  4. Anonymous
    2016-10-11T16:19:03+00:00

    Hi John,

    1. It's random. Sometimes new messages, sometimes replies. Sometimes only to another internal user, sometimes to external users. No pattern there.
    2. Nope. Again, totally random. Sometimes just a single line of text, other times there's a small attachment. No pattern here.
    3. The error is a smaller, black overlay that appears on screen in its own alert box, but not a traditional Mac OS pop-up alert. You don't need to hit "OK" or anything to dismiss (just the small close "x" in the top-right corner). It doesn't give the full error. To see the full error, I have to go to Window > Sync Errors. When I do, there are multiple errors (one for each error throughout the day/or until the user closes Outlook and restarts it). Same error over and over.
    4. No rules in play.

    I've contacted Microsoft. Their "solution" was to uninstall Office 2016 and delete and cache files, etc. associated with Office 2011 or 2016. Then reinstall Office 2016, setting up "new" from scratch. I did this. It made no difference. They asked me to do it again. It made no difference.

    Thanks,

    Kristin.

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