Microsoft 365 535 5.7.142
XOAUTH2 authentication failed
Microsoft 365 535 5.7.142 means: xOAUTH2 authentication failed. It is a permanent failure, so do not retry it unchanged. The fix is in the sending or receiving configuration named above, not in the list. Fix that, then resend.
Microsoft 365’s exact wording
Quoted from Microsoft Learn: Email non-delivery reports and SMTP errors in Exchange Online, checked 2026-11-05. Placeholders are Microsoft 365’s own.
Provider's description
XOAUTH2 authentication failed. Token will expire soon.
Possible cause
The OAuth access token that's used for authentication was close to expiration and was rejected. The client must request a new token, and retry authentication.
Provider's advice
Make sure that the session time doesn't exceed the token expiry time. Obtain a new OAuth token, if possible.
| Who sends it | Microsoft 365, Exchange Online and Outlook.com |
|---|---|
| Basic code | 535: Authentication credentials invalid (RFC) |
| Enhanced code | 5.7.142: Microsoft 365-specific, not in the IANA registry. Its subject digit puts it under 5.7.0 other or undefined security status. |
| Permanent or temporary | Permanent (5xx) |
| Verifying the list prevents it | No |
What the sender should do
The fix is in the sending or receiving configuration named above, not in the list. Fix that, then resend.
Would verifying the list have prevented Microsoft 365 535 5.7.142?
No
This reply is about your sending setup, the message or the receiving system, not about whether the address exists, so verifying the list will not prevent it.
Common questions
- What does Microsoft 365 535 5.7.142 mean?
- Microsoft 365 535 5.7.142 means: xOAUTH2 authentication failed. It is a permanent failure, so do not retry it unchanged. The fix is in the sending or receiving configuration named above, not in the list. Fix that, then resend.
- Should I retry after Microsoft 365 535 5.7.142?
- No. It is a permanent (5xx) failure, so the same message to the same address will fail again. Fix the cause first. The fix is in the sending or receiving configuration named above, not in the list. Fix that, then resend.
- Would verifying my list have prevented Microsoft 365 535 5.7.142?
- No. This reply is about your sending setup, the message or the receiving system, not about whether the address exists, so verifying the list will not prevent it.
Sources
- Microsoft Learn: Email non-delivery reports and SMTP errors in Exchange Online (checked 2026-11-05)
- RFC 4954: SMTP Service Extension for Authentication (checked 2026-11-05)
Registry and provider wording is quoted exactly; guidance is written by the SimpleVerifier Team.
SimpleVerifier Team · Last checked against the sources 2026-11-05