Issues with OpenSSL?

  • Resolved DJA_440

    (@dja_440)


    2 months, 4 weeks ago

    I have been an avid user of this plugin for years and it’s because it simply works. However i noticed over the last couple of days any site i had built with WP6.6 and the latest version of the plugin would simply fail regardless of where it’s sent from (pagebuilder, contact form 7, administrativ emails such as wordfence etc.)

    As these are production sites i had to get them back up and running asap, so i opened a conversation with the host who confirmed that nothing had changed their end. I updated certificates, made sure things were up to date and nothing worked. It was the same issue with over 10 sites.

    I have ended up with another mailer, not sure if i can name it but it effectively does exactly the same as WP SMTP but works seamlessly when configured with the same settings.

    The site is currently configured for SSL over port 587 and we force TLS with STARTTLS but i’m just flummoxed as to what has happened. Interestingly things are OK on a local install on a mac using local.wp so i’m not ruling out changes with the host quite yet… I snippet of the log here:

    Error Log ---
    SMTP Debug:
    2024-08-24 17:56:36 Connection: opening to mail.[REDACTED].com:587, timeout=30, options=array()

    2024-08-24 17:56:36 Connection: opened

    2024-08-24 17:56:36 SERVER -> CLIENT: 220-[REDACTED].io ESMTP Exim 4.97.1 #2 Sat, 24 Aug 2024 18:56:36 +0100 220-We do not authorize the use of this system to transport unsolicited, 220 and/or bulk e-mail.

    2024-08-24 17:56:36 CLIENT -> SERVER: EHLO [REDACTED].com

    2024-08-24 17:56:36 SERVER -> CLIENT: 250-gin.hostns.io Hello gin.hostns.io [109.70.148.37]250-SIZE 52428800250-8BITMIME250-PIPELINING250-PIPECONNECT250-AUTH PLAIN LOGIN250-STARTTLS250 HELP

    2024-08-24 17:56:36 CLIENT -> SERVER: STARTTLS

    2024-08-24 17:56:36 SERVER -> CLIENT: 220 TLS go ahead

    2024-08-24 17:56:36 Connection failed. Error #2: stream_socket_enable_crypto(): SSL operation failed with code 1. OpenSSL Error messages:error:1416F086:SSL routines:tls_process_server_certificate:certificate verify failed [[REDACTED]PHPMailer/SMTP.php line 488]

    SMTP Error: Could not connect to SMTP host. Connection failed. stream_socket_enable_crypto(): SSL operation failed with code 1. OpenSSL Error messages:error:1416F086:SSL routines:tls_process_server_certificate:certificate verify failed

    2024-08-24 17:56:36 CLIENT -> SERVER: QUIT

    2024-08-24 17:56:36

    2024-08-24 17:56:36

    2024-08-24 17:56:36 Connection: closed
Viewing 2 replies - 1 through 2 (of 2 total)
  • Plugin Support Darshana

    (@darshanaw)

    Hi @dja_440,

    Thank you for reaching out and for providing the detailed SMTP Debug log. The error message indicates an issue with the SSL certificate verification process while trying to connect to your email provider’s SMTP server.

    The particular line from the logs:

    SMTP Error: Could not connect to SMTP host. Connection failed. stream_socket_enable_crypto(): SSL operation failed with code 1. OpenSSL Error messages:error:1416F086:SSL routines:tls_process_server_certificate:certificate verify failed

    This suggests that the SSL/TLS handshake process, which encrypts your connection to the email server, failed due to problems with the server’s certificate verification. It may be due either to a server misconfiguration or an invalid/expired SSL certificate.

    Additionally, I also see the following message on your error log:

    We do not authorize the use of this system to transport unsolicited, 220 and/or bulk e-mail.

    Could you please get in touch with them again with the above information? They should be able to assist you accordingly.

    Let us know how it goes, or if you need more assistance!

    Thanks!

    I encountered this exact same problem. The issue was Norton 360 (the antivirus program). I disabled Auto-Protect, which in my past experience with Norton 360 disabled all protection. But not now. Disabling Auto-Protect still leaves some settings active. What causes the issue reported above with WP Mail SMTP was the Norton 360 outbound email scanning setting. As soon as I disabled it WP Mail SMTP worked perfectly!

Viewing 2 replies - 1 through 2 (of 2 total)
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