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We are required to monitor all in and out bound emails. we use ProofPoint. However, we want to send emails out from SalesForce but we need to monitor them with ProofPoint. Is there a way within SalesForce to send emails to the Office365 Exchange server which in turns sends out to ProofPoint?

I found this: https://www.cirrusinsight.com/blog/setting-email-relay-salesforce-office-365

I looks like that it is sending out from Office365 but it's not showing proofpoint in the headers at all.

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Yes. What you want to do is setup Email Relay. This will push all emails generated by SalesForce to your exchange server, which then relays them to the destination.

Best instructions are on the SalesForce configuration guide, here.

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