Cannot Authenticate SMTP

  • Resolved nablawave

    (@nablawave)


    1 month ago

    I just changed my email password on Outlook 365 and changed in your plugin Settings as well. The plugin is suddenly not working anymore. I changed Outlook password again but same error. Here’s the log:

    Versions:
    WordPress: 6.6.2
    WordPress MS: No
    PHP: 8.2.24
    WP Mail SMTP: 4.1.1

    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 3.1.1 30 May 2023

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

    SMTP Debug:
    2024-10-25 13:03:39 Connection: opening to smtp.office365.com:587, timeout=30, options=array()
    2024-10-25 13:03:39 Connection: opened
    2024-10-25 13:03:39 SERVER -> CLIENT: 220 AM0PR04CA0091.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 25 Oct 2024 13:03:39 +0000 [08DCF45D05A082A5]
    2024-10-25 13:03:39 CLIENT -> SERVER: EHLO www.nablawave.com
    2024-10-25 13:03:39 SERVER -> CLIENT: 250-AM0PR04CA0091.outlook.office365.com Hello [35.214.146.152]250-SIZE 157286400250-PIPELINING250-DSN250-ENHANCEDSTATUSCODES250-STARTTLS250-8BITMIME250-BINARYMIME250-CHUNKING250 SMTPUTF8
    2024-10-25 13:03:39 CLIENT -> SERVER: STARTTLS
    2024-10-25 13:03:39 SERVER -> CLIENT: 220 2.0.0 SMTP server ready
    2024-10-25 13:03:39 CLIENT -> SERVER: EHLO www.nablawave.com
    2024-10-25 13:03:39 SERVER -> CLIENT: 250-AM0PR04CA0091.outlook.office365.com Hello [35.214.146.152]250-SIZE 157286400250-PIPELINING250-DSN250-ENHANCEDSTATUSCODES250-AUTH LOGIN XOAUTH2250-8BITMIME250-BINARYMIME250-CHUNKING250 SMTPUTF8
    2024-10-25 13:03:39 CLIENT -> SERVER: AUTH LOGIN
    2024-10-25 13:03:39 SERVER -> CLIENT: 334 VXNlcm5hbWU6
    2024-10-25 13:03:39 CLIENT -> SERVER: [credentials hidden]
    2024-10-25 13:03:39 SERVER -> CLIENT: 334 UGFzc3dvcmQ6
    2024-10-25 13:03:39 CLIENT -> SERVER: [credentials hidden]
    2024-10-25 13:03:46 SERVER -> CLIENT: 535 5.7.139 Authentication unsuccessful, user password has expired. [AM0PR04CA0091.eurprd04.prod.outlook.com 2024-10-25T13:03:46.167Z 08DCF45D05A082A5]
    2024-10-25 13:03:46 SMTP ERROR: Password command failed: 535 5.7.139 Authentication unsuccessful, user password has expired. [AM0PR04CA0091.eurprd04.prod.outlook.com 2024-10-25T13:03:46.167Z 08DCF45D05A082A5]
    SMTP Error: Could not authenticate.
    2024-10-25 13:03:46 CLIENT -> SERVER: QUIT
    2024-10-25 13:03:46 SERVER -> CLIENT: 221 2.0.0 Service closing transmission channel
    2024-10-25 13:03:46 Connection: closed
    SMTP Error: Could not authenticate.
Viewing 1 replies (of 1 total)

  • Hi @nablawave,

    Thanks for reaching out!

    Recently, Microsoft updated their email service connections by removing Basic authentication. This change affects users trying to connect via their SMTP server using the “Other SMTP” mailer. Unfortunately, because of these changes on Microsoft’s end, we can’t re-enable Basic authentication. This change prevents SMTP plugins like ours as well as other software from being able to connect to Outlook over SMTP.

    The good news is that you can still connect to Outlook using the Outlook mailer in WP Mail SMTP Pro, which uses Modern authentication with OAuth2 for a secure connection. However, it’s important to note that Microsoft no longer supports this connection method for free accounts. If you have a paid Azure account, a Microsoft 365 account or other upgraded Microsoft account, you should still be able to create the necessary credentials for the Outlook mailer.

    Check out this guide in our documentation. It walks through setting up a connection to Outlook using the Outlook mailer, and includes screenshots of each step in the process: https://wpmailsmtp.com/docs/how-to-set-up-the-outlook-mailer-in-wp-mail-smtp/

    And in case it helps, we have a video walkthrough on setting up a connection to Outlook. The presenter goes over each step in the process, so you’re able to see exactly what they see as they connect: https://www.youtube.com/watch?v=A4IClPHbg3k

    I apologize for any inconvenience this may cause and appreciate your understanding.

    Thanks ??

Viewing 1 replies (of 1 total)
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