Cant send emails with SSL/TLS

  • Resolved Dave

    (@dhniels)


    5 years, 10 months ago

    I’m using gravity forms and for some reason my WP Mail SMTP plugin stopped working today. It says it cant connect to the SMTP server. Our mail server is in house. I triple checked the login info and ports. I validated that it wasn’t being blocked by the server or firewall. It doesn’t seem to even hit the server since the mail server logs don’t register anything. In Debug mode, wordpress doesn’t give any errors with SSL, but with TLS i did get this in my error.log:

    PHP Warning: stream_socket_enable_crypto(): SSL operation failed with code 1. OpenSSL Error messages:
    error:14090086:SSL routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify failed in /home/htdocs/wwwIRONNET/wp-includes/class-smtp.php on line 369

    The mailer works fine if I disable encryption entirely. The only changes I made recently was I updated all of our sites at ironcounty.net to a wildcard certificate, *.ironcounty.net (before, we had a like 10-12 individual certificates) so I deleted the old certs from the server and installed the new wildcard .crt and .key files, then updated the httpd.conf virtual host entries to point to the new crt, key, and chain files.

    I spent all day trying to figure this out. I ssh’ed into the server and was able to send successfully, so it seems like the only explanation is a wordpress issue, or something with the PHP mailer. Thoughts? I’m totally stumped.

    The page I need help with: [log in to see the link]

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  • I’m having the exact same problem. I also can’t send out emails unless I disable SSL/TLS and Auto TLS.

    Our mail server is with a company separate from our web hosting provider, but this hasn’t been a problem in the past with this plugin. I recently added Let’s Encrypt SSL certs if that means anything.

    Plugin Author Slava Abakumov

    (@slaffik)

    @dhniels @mdesk2
    You actually answered your own question when said about SSL changes made on a site. In short – server misconfiguration.

    Everything should be set up correctly in terms of certificates in both places (sender and receiver) to work correctly. It seems you’ve changed certificates on the sender (the server that is used to send an email from your WP install), but a software on a mail server (receiver) can’t negotiate a protocol to use to setup a secure connection.
    What you can try to do:
    1) try to make sure that both servers are using TLS v1.2 or higher, same protocol.
    2) read this section of the PHPMailer doc.

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