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Restrict Outbound Emails

zito2000 asked
Last Modified: 2020-03-25
Environment: On Prem Exchange 2013

I'm hoping this is an easy one.
If I have a user "John Smith" and I wanted to restrict his ability to send emails to ANYONE (whether internal or external emails) EXCEPT to his Manager, is there a way to do that?  I've been looking into transport rules, but can't seem to hammer down the correct configuration.

So to recap how it should work:
John sends an email to his manager --> Success
John sends an email to another internal employee --> Fails
John sends an email to an outside email address --> Fails
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