"Operation Failed" Error When Attempting to Send Email From Draft Folder in Outlook 2013

ConewagoAdmin
ConewagoAdmin used Ask the Experts™
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I have a user that encounters an "Operation Failed" error when sending emails from the Drafts folder in Outlook 2013. The email she is attempting to send usually have attachments (.pdf files), and this has been going on for some time. I have installed patches for Outlook, turned cache mode off, and turned it back on again, as well as disabled add-ins that I thought might be causing it. Not sure if it might be an Exchange Server user profile issue, but it only seems to happen to this user.
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FOXActive Directory/Exchange Engineer
Top Expert 2015
Commented:
Check to see if the email can send when they are using OWA.  If so the problem is on the client side.

Author

Commented:
Foxluv,

The messages in question were not able to be saved to drafts, so they were not accessible In OWA. I have been trying to find a solution to this, but have only been able to deduce that the cause seems to stem from the user's reliance on Outlook templates that have been corrupted. I've never seen anything like this, and it doesn't happen to any of our other users.

Thanks for your help.
FOXActive Directory/Exchange Engineer
Top Expert 2015
Commented:
Have her create an email and have her save it as a .msg file instead.  After she saves it have her open it up and add an attachment and see if it sends.
After conducting what felt like an inquisition, I was able to determine it was the email templates the user had saved on her desktop. After deleting those, and starting fresh, the problem disappeared. Thank you for your help, Foxluv.

Author

Commented:
The user was withholding information, so after getting all of the details, I was able to use the suggestions offered by Foxluv to assist in the troubleshooting, and eventual solution of the issue.

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