drew4

Thanks for the quick reply!

I was speaking with Broadbean and they weren’t able to to tell me this – thank you for highlighting how things work!

It’s a bizarre setup from Broadbean to require essentially spoofed FROM addresses.

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For anyone else who finds this:

We were able to solve the problem by keeping the relay enabled but forcing the “FROM” address to be the one of the relay account itself (via Office 365). The relay was blocking the emails as the FROM address appeared spoofed so it hit the exchange security.

Doing this allows all emails to be send via the relay and to Broadbean – however Broadbean will not send a notification to the applicant as it doesn’t understand the FROM address (again, odd setup they have). But you can hook into the WP Broadbean action and send your own custom notification to solve this!

Thanks again Mark 🙂