Office 365 not receiving email from domain when sent externally

I am trying to get a Word Press site to send email to my domain, with a FROM address of my domain, but it is only sending the email to the address setup outside of the domain.
We use Exchange 365.

"Notification: Send email to" is setup with two users: me@gmail.com, and me@domain.com
"Notification: From email" is group@domain.com (I have tried specific user as well)
I receive the notification correctly at @gmail.com, but not @domain.com.

I have tried adding group@domain.com to the Allow list, but that did not work.

What could be stopping me from receiving it at the @domain.com addresses?
jjwolvenAsked:
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Vasil Michev (MVP)Commented:
Probably it's being marked as spam on O365 side. If this is the case, you might want to update your SPF record to include the sender servers. Have you run a Message trace to confirm it did arrive at O365 servers?
jjwolvenAuthor Commented:
I have already added the From address as a safe sender.
How can I tell if a message is blocked in O365?
Vasil Michev (MVP)Commented:
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jjwolvenAuthor Commented:
I already tried this. The message sent to there did not show up at all; it was blocked somewhere before there but made it through to gmail.com.
Vasil Michev (MVP)Commented:
So try to get the trace on the sending side. If the app you are using is trying to relay the message as a specific user, it needs to be able to authenticate to O365, and also must support TLS.

You can always set up forwarding from the gmail address to O365 if nothing else works.
jjwolvenAuthor Commented:
Fowarding is a workaround, not a solution.

Figured out the issue, the issue was on the sending side. Authentication had not been setup correctly.

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jjwolvenAuthor Commented:
It was the solutions.
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