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5.7.57 Client was not authenticated to send anonymous mail during MAIL FROM

Provider: Microsoft 365 / Outlook

Sample bounce line

530 5.7.57 Client was not authenticated to send anonymous mail during MAIL FROM [AM0PR0102CA0070.eurprd01.prod.exchangelabs.com]

What it means

An application or device was configured to relay through smtp.office365.com but did not authenticate, so Microsoft refused the MAIL FROM command. Microsoft's explanation is that the configuration of the application or device is at fault, not the mailbox.

Why it happens

How to fix it

  1. Enable SMTP AUTH for the specific mailbox the device uses, rather than for the whole tenant.
  2. Give the device a real sign-in: username, password and STARTTLS on port 587.
  3. Where the device cannot do modern authentication, use a dedicated mailbox for it and keep its credentials current.
  4. If the device only needs to send to recipients inside your own tenant, direct send or a connector may be the right route instead of authenticated submission.

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Official documentation

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