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Unable to Send Email "Word Template Assigned" Error

Okay, so this is a bit of a weird one and not sure what the problem is. Our client's emailing word templates has been setup for forever. Last Saturday, it just stopped working. They sent emails on Saturday and then on Tuesday they could no longer do so.

They could not send emails through their live GP company. I had a backup of the live company from about a month ago so restored it to the test and I tested sending emails from there. It also didn't work. This leads me to believe that the issue was not within GP but some outside force.

The user was not even getting the prompt to enter her email and password. I had GP run as administrator and that fixed that issue. She was able to enter her email and password. When she goes to email the word template, it fails and says that no word template has been applied. The weird thing about this is that A) I can print the word template report directly and B) when she runs the email process, it generates the pdf document to her temp folder and then fails to send it. The error message she receives is "A word template must be assigned before sending this document"

I have tried everything I could find to fix the issue. I have removed the reply contact on the message. I tried removing the email template completely. I have tried unapplying and reapplying the word templates. I have ran both GP and outlook as administrator. I don't think that this issue is an Office 365 update problem because I looked at her computer and her outlook hasn't updated in a while. GP has definitely not been updated in the last week.

Any ideas?

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Microsoft Dynamics GP

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