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How to require confirmation on sending external emails with attachments

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Does anyone know of a way to require a user to confirm sending (via pop-up) of an email that is 

a) addressed to an external domain

b) contains an attachment

I have tried to set up the Policy Tips rule in mail flow, but it doesn't not work with selecting an external contact and attachment size > 1kb. It says you can only use Policy Tips when selecting mail contains sensitive information. 

Thank you in advanced for any advice!


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