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Error 5.7.57 SMTP

When I configure my Orion NPM "Default Send Email Action" I specify a return email address (Office 365 distribution group) that authenticates with a specific mailbox that has "Send As" permission for the distribution group. When I "Send Test Email", everything works great and I receive the email as a member of the distribution group. However, when I am supposed to get a real alert, I get an error:

"Sending the email to %DistributionGroup% with subject ALERT: %ServerHostname% has rebooted. using SMTP Server smtp.office365.com failed. The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM"

  • I am not attempting to send anonymous mail.
  • Test email works and I receive the message so authentication is not the issue.
  • Yes, we are using TCP\587 TLS.

Does anyone have an idea why this might be the case?

Thank you,

Scott Shackleton