Authentication unsuccessful

  • Resolved rtnlsltn

    (@rtnlsltn)


    3 years, 1 month ago

    Last Thursday the password was changed to the account this plugin uses without my knowledge. A number of emails had failed over the 4 days this persisted. I was informed of the new password today and changed it, but am still getting an authentication error. There is no 2FA enabled, the Azure Privacy Defaults are disabled, and nothing else has changed. This has been configured for about 8 months without issues, until today. I contacted the mail provider to ensure the webserver was not on a blacklist. I am able to login to the account through outlook without issues. I also ran a blacklist check on the site and it’s clean.

    I don’t necessarily think this is a plugin issue, but any help to resolve would be great!

    Versions:
    WordPress: 6.2
    WordPress MS: No
    PHP: 8.0.28
    WP Mail SMTP: 3.7.0

Params:
    Mailer: smtp
    Constants: No
    ErrorInfo: SMTP Error: Could not authenticate.
    Host: smtp.office365.com
    Port: 587
    SMTPSecure: tls
    SMTPAutoTLS: bool(true)
    SMTPAuth: bool(true)

Server:
    OpenSSL: OpenSSL 1.1.1t 7 Feb 2023

Debug:
    Email Source: Returns Management
    Mailer: Other SMTP
    SMTP Error: Could not authenticate.
    Email Source: WP Mail SMTP
    Mailer: Other SMTP
    SMTP Error: Could not authenticate.

SMTP Debug:
    2023-04-04 18:13:26 Connection: opening to smtp.office365.com:587, timeout=300, options=array()

2023-04-04 18:13:26 Connection: opened

2023-04-04 18:13:26 SERVER -> CLIENT: 220 BN8PR16CA0034.outlook.office365.com Microsoft ESMTP MAIL Service ready at Tue, 4 Apr 2023 18:13:25 +0000

2023-04-04 18:13:26 CLIENT -> SERVER: EHLO redacted.com

2023-04-04 18:13:26 SERVER -> CLIENT: 250-BN8PR16CA0034.outlook.office365.com Hello [2600:3c00::f03c:93ff:fefb:bd2b]250-SIZE 157286400250-PIPELINING250-DSN250-ENHANCEDSTATUSCODES250-STARTTLS250-8BITMIME250-BINARYMIME250-CHUNKING250 SMTPUTF8

2023-04-04 18:13:26 CLIENT -> SERVER: STARTTLS

2023-04-04 18:13:26 SERVER -> CLIENT: 220 2.0.0 SMTP server ready

2023-04-04 18:13:26 CLIENT -> SERVER: EHLO redacted.com

2023-04-04 18:13:26 SERVER -> CLIENT: 250-BN8PR16CA0034.outlook.office365.com Hello [2600:3c00::f03c:93ff:fefb:bd2b]250-SIZE 157286400250-PIPELINING250-DSN250-ENHANCEDSTATUSCODES250-AUTH LOGIN XOAUTH2250-8BITMIME250-BINARYMIME250-CHUNKING250 SMTPUTF8

2023-04-04 18:13:26 CLIENT -> SERVER: AUTH LOGIN

2023-04-04 18:13:26 SERVER -> CLIENT: 334 VXNlcm5hbWU6

2023-04-04 18:13:26 CLIENT -> SERVER: [credentials hidden]

2023-04-04 18:13:26 SERVER -> CLIENT: 334 UGFzc3dvcmQ6

2023-04-04 18:13:26 CLIENT -> SERVER: [credentials hidden]

2023-04-04 18:13:35 SERVER -> CLIENT: 535 5.7.139 Authentication unsuccessful, the user credentials were incorrect. [BN8PR16CA0034.namprd16.prod.outlook.com 2023-04-04T18:13:35.390Z 08DB30B04C54A8E4]

2023-04-04 18:13:35 SMTP ERROR: Password command failed: 535 5.7.139 Authentication unsuccessful, the user credentials were incorrect. [BN8PR16CA0034.namprd16.prod.outlook.com 2023-04-04T18:13:35.390Z 08DB30B04C54A8E4]

SMTP Error: Could not authenticate.

2023-04-04 18:13:35 CLIENT -> SERVER: QUIT

2023-04-04 18:13:35 SERVER -> CLIENT: 221 2.0.0 Service closing transmission channel

2023-04-04 18:13:35 Connection: closed

SMTP Error: Could not authenticate.

    • This topic was modified 3 years, 1 month ago by rtnlsltn.
    • This topic was modified 3 years, 1 month ago by rtnlsltn.
Viewing 6 replies - 1 through 6 (of 6 total)
  • Plugin Support Dake

    (@dakeg)

    3 years, 1 month ago

    Hi @rtnlsltn

    Thanks for creating your own thread.

    You mentioned creating a new password, but was it an app password? that is necessary for connecting to the Outlook SMTP.

    The “Password command failed” error message specifically appears, so even if you have not done this before, please generate a new APP Password and replace the password in your WP Mail SMTP settings.

    Please search for the “Generating an App Password in Outlook” section in our documentation.

    If somehow this issue persists, to confirm if this is a server-specific issue, please try connecting to a different SMTP server using one of the other connections mentioned in our Other SMTP documentation.

    If the issue persists, please try setting up a different mailer for testing purposes.

    The easiest mailers to set up for testing purposes(outside of the Other SMTP mailer) are the Google (free) and Sendinblue (free tier) mailers.

    Thread Starter rtnlsltn

    (@rtnlsltn)

    3 years, 1 month ago

    I’ve created an app password, but am receiving the same error.

    Attempted using a different plugin, same error.

    Other sites on the same VPS are not having issues sending via the same port w/TLS. However, those sites are not using Office 365 emails.

    Moving onto the next steps.

    • This reply was modified 3 years, 1 month ago by rtnlsltn.
    • This reply was modified 3 years, 1 month ago by rtnlsltn.
    Plugin Support Dake

    (@dakeg)

    3 years, 1 month ago

    Hi @rtnlsltn

    If you run into the same issue using different SMTP plugins that implies there may be an issue with the credentials or you may need to reach out to your website host about this issue.

    This of course in in addition to the other troubleshooting steps I mentioned above.

    Thread Starter rtnlsltn

    (@rtnlsltn)

    3 years, 1 month ago

    Alternate accounts work. I was also able to confirm that the ‘broken’ account also errors on another site that’s on a different VPS server. Definitely something suspect upstream with either GoDaddy or Outlook/365. Currently unclear on root cause….

    Not sure what else to do, GoDaddy is saying nothing is wrong and we’re not on any blacklists.

    Plugin Support Dake

    (@dakeg)

    3 years, 1 month ago

    Hi @rtnlsltn

    Thanks for getting back to us. You can also try reaching out to Microsoft/Outlook support about this issue. But the easiest workaround in the meantime would be to use a different mailer while you wait on their support teams to look into and resolve this issue.

    I’m sorry to say that this is not an issue that we can resolve from our end.

    Thread Starter rtnlsltn

    (@rtnlsltn)

    3 years, 1 month ago

    I think that’s the next step. The strangest thing is that the account worked for ~16 hours randomly, then stopped working again. No change to anything during that time.

    Thanks for looking into this.

Viewing 6 replies - 1 through 6 (of 6 total)

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