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Distribution group tracking external contacts.

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I have a distribution group that receives email from an external source then forwards to some internal and some external users.  everyone in the group gets the emails except one single external user. 

I can send an email to the user from my email on the same domain as the DG.

Other users from his company are getting the emails with no problems.

He has searched all folders for the messages as well as the junk folders.

I have deleted and recreated his external contact from office365.

My issue is that i cannot verify the message left our system. How can i track it if its being sent to a DG email address. is there a way to show each individual the message is sent to in the dg and confirm that it was in fact sent from office365.

Any help would be great. I'm sorta at the end of my ideas.
THANKS!


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