I'm trying to disable Direct Send in Exchange due to issues with how Zendesk interacts with our email environment. I couldn't turn it off completely, but I created a transport rule to block all spoof emails based on Microsoft's guidance. The rule states that if an email is received from outside our organization and the sender's domain is contoso.com, it should be directed to hosted quarantine, unless specific message headers are involved. However, a user recently reported that their email was broken. After looking into it, I discovered that it was a Zoom meeting invite they had forwarded, and Exchange tagged it as coming from 'Outside the organization.' I'm concerned that there's an unusual interaction with the Zoom plugin in Outlook causing these calendar items to misroute. What can I do to resolve this issue?
3 Answers
It's not too complex to manage this. You might want to check out the Zendesk Exchange connector to keep Direct Send disabled. It does involve some changes, but maybe it could help streamline things instead of dealing with unpredictable transport rules.
In our case, we had to allow that header, but we were careful since malicious parties were sending meeting invites. Just be cautious with the exceptions you create, especially with types of meeting forwards!
I faced a similar issue and found that adding an exception for the 'X-MS-Exchange-MeetingForward-Message' header, specifically matching 'Forward', helped get the forwarding to work again. It seemed to stop other notifications too, so I had to create a new connector, but it was worth it to keep Direct Send disabled.

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