exchange alert for external recipients for specfified internal groups of users

We are using Exchange 2013 in a hybrid config with O365

We have a requirement to use the exchange mailtips function to notify users when sending to email accounts outside of the organisation.

However, we need to be able to specify which internal user/groups this alert is active on, for example: the procurement team would not want the alert on, however, the finance team would.

Is this even possible?
D BAsked:
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IvanSystem EngineerCommented:

it is posible to be done via server rules. You can create rule that applied to senders from finance, so when they send email outside the organization they will receive Mail Tip.

Take a look at picture. In this example I have selected to inform all users in organization, but you can simple choose a group in stead.

D BAuthor Commented:

thanks for the quick response

When we try it, the rules won't save due to the following additional requirement, have I missed something?mailtip error
IvanSystem EngineerCommented:

yeah, it seams you must configure that parameter as well. I think you can create custom DLP to include any type of email sent from that group, but have to test it.


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