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Christian HansFlag for United States of America

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O365 Mail Routing (Hop count exceeded - possible mail loop ATTR1)

I'm experiencing some issues in out Office 365 Hybrid environment...

Strangely, out of the few thousand users, there is a very small handful of users that people who have mailboxes in O365 get the following NDR when emailing them.


Sender:                Cal.Naughton@contoso.com (mailbox in O365)
Recipient:            Ricky.Bobby@contoso.com (Mailbox On Premises - myexch2013server.contoso.com)


BN3NAM01FT032.mail.protection.outlook.com rejected your message to the following e-mail addresses:
Ricky.Bobby@contoso.mail.onmicrosoft.com

BN3NAM01FT032.mail.protection.outlook.com gave this error:
Hop count exceeded - possible mail loop ATTR1 [BN3NAM01FT032.eop-nam01.prod.protection.outlook.com]
A problem occurred during the delivery of this message. Please try to resend the message later.

Diagnostic information for administrators:
Generating server: myexch2013server.contoso.com
Ricky.Bobby@contoso.mail.onmicrosoft.com

BN3NAM01FT032.mail.protection.outlook.com #554 5.4.14 Hop count exceeded - possible mail loop ATTR1 [BN3NAM01FT032.eop-nam01.prod.protection.outlook.com] ##rfc822;Ricky.Bobby@contoso.mail.onmicrosoft.com


Recipient SMTP:Ricky.Bobby@contoso.com does have an email alias on-prem of smtp:Ricky.Bobby@contoso.mail.onmicrosoft.com but doesnt have a Target Address stamped. So I would think it wouldn't be sending the message back to ExOL etc.


I don't know where to start troubleshooting, this is only happening when cloud users try emailing to 5 users that are on prem. SO that would rule out DNS and connectors I would think, since it works fine for the other thousands when sending On-Prem > Cloud and Cloud > On-Prem.

Any ideas? Thanks in advance.
Avatar of Adam Brown
Adam Brown
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Check the O365 domain.com domain settings. Check it to see if the domain is set to Authoritative. If it is, you'll want to switch it to Internal Relay and make sure there's a send connector configured to send messages to onprem using the @domain.com domain.
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Avatar of Sunil Chauhan
Sunil Chauhan
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