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Hi
We have Exchange server 2013 with Edge server 2010 (I know, this is not conventional), for some time now, sending emails to our partners with an Office 365 messaging system has not been received, the strangest thing that if the message is new (new message), it arrives at destination, but if it is a reply or thread, the message does not arrive, knowing that our domain and Ip mx are not blacklisted. Apart from a partner who added our domain to their list of trusted domains, the problem persists for others.
thanks
regards
What does message tracking show?
Hi
the message exit our organisation (exit our EDGE), with Receipient Status 250 2.1.5 Recipient OK, after there is not a NDR returned.
regards
Is that it? You should see more in the protocol logs. You should the message sent and then a QUIT and 221 Closing session
If you see all that and 365 accepted the message, then you need to look in 365 message tracking to see what happens next.
Does Exchange Message tracking show the message sent? Can you post that here minus any personal info?
From our Side : 
Ok, that indicates the messages were accepted on the 365 side then ( THE SEND status)
Can you do a message trace on the ones that werent received on the 365 side?
We were able to track the message on the other side, we noticed that sometimes the message is received (blank message without body and subject), but in most cases, it is quarantined or classified as spam, if the domain is added to the whitelist (trusted domain), the problem will be solved, we cannot ask all the organizations to add us, especially the large ones. the question is: why some of our emails are considered as junk, especially since our domain is not in the blacklist?
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Have you publish DKIM and DMARC record? https://social.technet.microsoft.com/wiki/contents/articles/35595.on-premises-exchange-dkim-and-dmarc-setup.aspx
You could find some clues on o365 side, check the quarantine reason: https://learn.microsoft.com/en-us/microsoft-365/security/office-365-security/manage-quarantined-messages-and-files?view=o365-worldwide#view-quarantined-message-details
Finally, by implementing DKIM, the problem seems to be solved, thanks for your support.
Please mark the helpful suggestions as answer to highlight it, thanks.
So you have confirmed the issue occur with several O365 domains, and you cannot reply messages from all of them except one who added you to trusted domains?
Check the message header from them, does it contain "Reply-to" which is different from "From"?
Please track the "reply" message from O365 side, compare the results with "send" message and see what's the difference: https://www.codetwo.com/admins-blog/message-tracking-office-365/
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I confirm that the issue occur with several O365 domains, and in most cases, I can not send message to them (some time the message is received), except who added us to trusted domains. Miscrosoft Support said that all is ok in our side.
We were able to track the message on the other side, the rejected messages are quarantined or classified as spam, Why? our domain and our IP of our MX are not Blacklisted.