Exchange Mailtips for Emails Containing Attachments and Directed to External Recipient

Question

Hello Everyone!&nbsp;I'm trying to setup a global MailTip or alert which would notify a user when they are sending an e-mail containing attachments to an external recipient.I'm trying to weigh all the possibilities available and so far I've seen options with exchange MailTips and Purview DLP policies. I have played a little bit with MailTips and turned on the "-MailTipsExternalRecipientsEnabled" option with PowerShell. This works great but only addresses half of my want list. Is there a way to modify this MailTip rule to apply only when the email contains an attachment? Not seeing too much on the official MS documentation, unless I'm not looking in the right place.&nbsp;If not doable via MailTips, does anyone have any other suggestion to do this?

vasilmichev · Answer

That's not doable. Mailtips cannot detect this scenario (and cannot be modified), and DLP will only work for items containing sensitive data.

sirfabs · Answer

sirfabs&nbsp;&nbsp;Tested in purview and DLP policies seem to be able to do this with a tooltip.

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Exchange Mailtips for Emails Containing Attachments and Directed to External Recipient

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