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Azure VM using SMTP

John Rafter 81 Reputation points
2022-01-27T18:32:56.903+00:00

Current Azure VM was using smtp.xyz.com to send emails internally. We have since migrated from the 2013 server to a 2016 server to be used for management purposes only. We added a CNAME record for smtp.xyz.com to point to xyz-com.mail.protection.outlook.com but emails are not being delivered. Does one need a different setup?

Reviewing the errors below:

Error in processing. The server response was: 4.4.4 Temporary server error. Please try again later ATTR5
System.Net.Mail.SmtpException: Error in processing. The server response was: 4.4.4 Temporary server error. Please try again later ATTR5 [xxxxxxxx.eop-nam11.prod.protection.outlook.com

Exchange | Exchange Server | Management
Exchange | Exchange Server | Management

The administration and maintenance of Microsoft Exchange Server to ensure secure, reliable, and efficient email and collaboration services across an organization.

Exchange | Hybrid management
Exchange | Hybrid management

The administration of a hybrid deployment that connects on-premises Exchange Server with Exchange Online, enabling seamless integration and centralized control.


Answer accepted by question author

Andy David - MVP 160.3K Reputation points MVP Volunteer Moderator
2022-01-27T18:54:58.917+00:00

From that, I'd say you are being greylisted by 365. Did the external sending IP change when you migrated to a new server? Is the cert used on the 2016 cert correctly applied to the send connector and matching the FQDN?

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