I'm managing a WordPress site that sends email notifications whenever a customer places an order. The notifications are working fine as they reach other email addresses, but for the Office 365 tenant we're managing, the emails aren't delivering. I've tried several things, like setting up mail flow rules to allow emails from the WordPress site's domain and IP address, as well as adding it to the allowed domain list and creating a connector for the site's IP. Unfortunately, none of these steps have helped. I want to find a solution without resorting to a paid SMTP plugin, as I believe there has to be a way to allow these emails through the spam filter since I can receive them on my own Office 365 account.
2 Answers
You might need to check where those emails that are failing are bouncing back to. Office 365 can be really strict with IP addresses when it comes to sending mail. Look for any bounce messages that might provide clues on what’s going wrong.
Have you checked if those emails are sitting in quarantine? Sometimes emails get caught in there if the service thinks they are spam.

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