In EXCHANGE 365,  I need to Flag any mail going to

Lenny Cordisco
Lenny Cordisco used Ask the Experts™
I was asked by my CEO if I can monitor any mail that is going to one of our competitors.

Someone in my organization is leaking information to one of our competitors.

Here is what I want to do.   I want to create a flag or notification when someone in our company/domain sends an email to one of our competitors.

Ultimately I want to see a copy of the message but I do not want the end users to know about it.
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Brian BEE Topic Advisor, Independant Technology Professional

If your outbound email goes direct from your Exchange server, the easiest way to find this might be via your firewall logs. That will also give you some historic information as well in case the individual has stopped already.
Of course keep in mind this will only help if the individual is sending via your company's mail server. If they were smart, they wouldn't be doing that anyway.
Todd NelsonSystems Engineer
Top Expert 2016

Ronin provided some good references.

Keep in mind that the information being "leaked" may not be through email or even from your email domain.  With that said, you should be able to easily create a mail flow rule in the EAC to send a copy of any email based on recipient addresses.

If you are currently configured for hybrid, make sure to create the rule both on premises and in EXO.
Lenny CordiscoIT Manager


Thanks Guys,    ....and yes.   I am aware that the leak may not be happening through our mail system.   In fact, I advised the CEO that aside from adding rule on the mail server, there may be no way to figure this out.  Most people use personal email and cell phones as well.  

I would like to think that people are smart and would know not correspond with a competitor through our mail system...  

Gonna see if I can set that up now.

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