XF 2.3 Emails not being sent wrong openSSL version

O

Onlyme

Active member
Hi all,

After upgrading to the latest version of xenforo emails are no longer being delivered and has a wrong openSSL error.

Service I'm using: https://www.servermx.com/en/help/howto/email-client/client-configuration-with-encryption/

Php 8.3 and the panel is reporting OpenSSL 3.0.2 15 Mar 2022. Ports 587 & 687 not working and I have no idea what to do ☹️

Symfony\Component\Mailer\Exception\TransportException: Email to myemail@proton.me from admin@mysite.com failed: Connection could not be established with host "ssl://smtp.servermx.com:587": stream_socket_client(): SSL operation failed with code 1. OpenSSL Error messages: error:0A00010B:SSL routines::wrong version number src/vendor/symfony/mailer/Transport/Smtp/Stream/SocketStream.php:154
Generated by: admin Oct 28, 2025 at 2:32 PM
#0 [internal function]: Symfony\Component\Mailer\Transport\Smtp\Stream\SocketStream->Symfony\Component\Mailer\Transport\Smtp\Stream\{closure}(2, 'stream_socket_c...', 's...', 157)
#1 src/vendor/symfony/mailer/Transport/Smtp/Stream/SocketStream.php(157): stream_socket_client('ssl://smtp.serv...', 0, '', 60, 4, Resource id #4)
#2 src/vendor/symfony/mailer/Transport/Smtp/SmtpTransport.php(251): Symfony\Component\Mailer\Transport\Smtp\Stream\SocketStream->initialize()
#3 src/vendor/symfony/mailer/Transport/Smtp/SmtpTransport.php(194): Symfony\Component\Mailer\Transport\Smtp\SmtpTransport->start()
#4 src/vendor/symfony/mailer/Transport/AbstractTransport.php(72): Symfony\Component\Mailer\Transport\Smtp\SmtpTransport->doSend(Object(Symfony\Component\Mailer\SentMessage))
#5 src/vendor/symfony/mailer/Transport/Smtp/SmtpTransport.php(136): Symfony\Component\Mailer\Transport\AbstractTransport->send(Object(Symfony\Component\Mailer\SentMessage), Object(Symfony\Component\Mailer\DelayedEnvelope))
#6 src/XF/Mail/Mailer.php(329): Symfony\Component\Mailer\Transport\Smtp\SmtpTransport->send(Object(Symfony\Component\Mime\Email))
#7 src/XF/Mail/Mail.php(576): XF\Mail\Mailer->send(Object(Symfony\Component\Mime\Email), Object(Symfony\Component\Mailer\Transport\Smtp\EsmtpTransport))
#8 src/XF/Admin/Controller/ToolsController.php(309): XF\Mail\Mail->send(Object(Symfony\Component\Mailer\Transport\Smtp\EsmtpTransport), false)
#9 src/XF/Mvc/Dispatcher.php(362): XF\Admin\Controller\ToolsController->actionTestEmail(Object(XF\Mvc\ParameterBag))
#10 src/XF/Mvc/Dispatcher.php(264): XF\Mvc\Dispatcher->dispatchClass('XF:Tools', 'TestEmail', Object(XF\Mvc\RouteMatch), Object(XF\Admin\Controller\ToolsController), NULL)
#11 src/XF/Mvc/Dispatcher.php(121): XF\Mvc\Dispatcher->dispatchFromMatch(Object(XF\Mvc\RouteMatch), Object(XF\Admin\Controller\ToolsController), NULL)
#12 src/XF/Mvc/Dispatcher.php(63): XF\Mvc\Dispatcher->dispatchLoop(Object(XF\Mvc\RouteMatch))
#13 src/XF/App.php(2824): XF\Mvc\Dispatcher->run()
#14 src/XF.php(806): XF\App->run()
#15 admin.php(15): XF::runApp('XF\\Admin\\App')
#16 {main}
 
Last edited:
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Onlyme said:
Hi all,

After upgrading to the latest version of xenforo emails are no longer being delivered and has a wrong openSSL error.

Service I'm using: https://www.servermx.com/en/help/howto/email-client/client-configuration-with-encryption/

Php 8.3 and the panel is reporting OpenSSL 3.0.2 15 Mar 2022. Ports 587 & 687 not working and I have no idea what to do ☹️

Symfony\Component\Mailer\Exception\TransportException: Email to myemail@proton.me from admin@mysite.com failed: Connection could not be established with host "ssl://smtp.servermx.com:587": stream_socket_client(): SSL operation failed with code 1. OpenSSL Error messages: error:0A00010B:SSL routines::wrong version number src/vendor/symfony/mailer/Transport/Smtp/Stream/SocketStream.php:154
Generated by: admin Oct 28, 2025 at 2:32 PM
#0 [internal function]: Symfony\Component\Mailer\Transport\Smtp\Stream\SocketStream->Symfony\Component\Mailer\Transport\Smtp\Stream\{closure}(2, 'stream_socket_c...', 's...', 157)
#1 src/vendor/symfony/mailer/Transport/Smtp/Stream/SocketStream.php(157): stream_socket_client('ssl://smtp.serv...', 0, '', 60, 4, Resource id #4)
#2 src/vendor/symfony/mailer/Transport/Smtp/SmtpTransport.php(251): Symfony\Component\Mailer\Transport\Smtp\Stream\SocketStream->initialize()
#3 src/vendor/symfony/mailer/Transport/Smtp/SmtpTransport.php(194): Symfony\Component\Mailer\Transport\Smtp\SmtpTransport->start()
#4 src/vendor/symfony/mailer/Transport/AbstractTransport.php(72): Symfony\Component\Mailer\Transport\Smtp\SmtpTransport->doSend(Object(Symfony\Component\Mailer\SentMessage))
#5 src/vendor/symfony/mailer/Transport/Smtp/SmtpTransport.php(136): Symfony\Component\Mailer\Transport\AbstractTransport->send(Object(Symfony\Component\Mailer\SentMessage), Object(Symfony\Component\Mailer\DelayedEnvelope))
#6 src/XF/Mail/Mailer.php(329): Symfony\Component\Mailer\Transport\Smtp\SmtpTransport->send(Object(Symfony\Component\Mime\Email))
#7 src/XF/Mail/Mail.php(576): XF\Mail\Mailer->send(Object(Symfony\Component\Mime\Email), Object(Symfony\Component\Mailer\Transport\Smtp\EsmtpTransport))
#8 src/XF/Admin/Controller/ToolsController.php(309): XF\Mail\Mail->send(Object(Symfony\Component\Mailer\Transport\Smtp\EsmtpTransport), false)
#9 src/XF/Mvc/Dispatcher.php(362): XF\Admin\Controller\ToolsController->actionTestEmail(Object(XF\Mvc\ParameterBag))
#10 src/XF/Mvc/Dispatcher.php(264): XF\Mvc\Dispatcher->dispatchClass('XF:Tools', 'TestEmail', Object(XF\Mvc\RouteMatch), Object(XF\Admin\Controller\ToolsController), NULL)
#11 src/XF/Mvc/Dispatcher.php(121): XF\Mvc\Dispatcher->dispatchFromMatch(Object(XF\Mvc\RouteMatch), Object(XF\Admin\Controller\ToolsController), NULL)
#12 src/XF/Mvc/Dispatcher.php(63): XF\Mvc\Dispatcher->dispatchLoop(Object(XF\Mvc\RouteMatch))
#13 src/XF/App.php(2824): XF\Mvc\Dispatcher->run()
#14 src/XF.php(806): XF\App->run()
#15 admin.php(15): XF::runApp('XF\\Admin\\App')
#16 {main}
Click to expand...
Please try this solution already posted by @Sim, here.
 
Upvote 0 Downvote
Onlyme said:
Thanks for the information but I've already seen that thread and it didn't work.
Click to expand...
At the very least, it looks like you should be on port 587 and it's confirmed to be STARTTLS

Code: 
220 ns12.servermx.com mail server [110 ms]
EHLO [redacted]
250-ns12.servermx.com Hello [redacted] [xxx.xxx.xxx.53]
250-SIZE 52428800
250-8BITMIME
250-DSN
250-AUTH PLAIN LOGIN
250-STARTTLS
250 HELP [145 ms]

This is usually the result of mis-matched configuration and use of TLS and STARTTLS. If this was working before, the OpenSSL version shouldn't be a factor in this case.
 
Upvote 0 Downvote
ENF said:
At the very least, it looks like you should be on port 587 and it's confirmed to be STARTTLS

Code: 
220 ns12.servermx.com mail server [110 ms]
EHLO [redacted]
250-ns12.servermx.com Hello [redacted] [xxx.xxx.xxx.53]
250-SIZE 52428800
250-8BITMIME
250-DSN
250-AUTH PLAIN LOGIN
250-STARTTLS
250 HELP [145 ms]

This is usually the result of mis-matched configuration and use of TLS and STARTTLS. If this was working before, the OpenSSL version shouldn't be a factor in this case.
Click to expand...
What would you recommend is this situation? Is the issue the provider?
 
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Onlyme said:
What would you recommend is this situation? Is the issue the provider?
Click to expand...
Do you have access to SSH on your server? If so, you can run this command to test the connection:

openssl s_client -connect smtp.servermx.com:587 -starttls smtp

Running this command on my side, nets the following results, which means that the connection between the server and the smtp host is working.
If this does not work, then you'd need to speak to whomever operates your server for assistance.

Code: 
[root@enf ~]# openssl s_client -connect smtp.servermx.com:587 -starttls smtp
CONNECTED(00000003)
depth=3 C = GB, ST = Greater Manchester, L = Salford, O = Comodo CA Limited, CN = AAA Certificate Services
verify return:1
depth=2 C = US, ST = New Jersey, L = Jersey City, O = The USERTRUST Network, CN = USERTrust RSA Certification Authority
verify return:1
depth=1 C = GB, ST = Greater Manchester, L = Salford, O = Sectigo Limited, CN = Sectigo RSA Domain Validation Secure Server CA
verify return:1
depth=0 CN = *.servermx.com
verify return:1
---
Certificate chain
 0 s:/CN=*.servermx.com
   i:/C=GB/ST=Greater Manchester/L=Salford/O=Sectigo Limited/CN=Sectigo RSA Domain Validation Secure Server CA
 1 s:/C=GB/ST=Greater Manchester/L=Salford/O=Sectigo Limited/CN=Sectigo RSA Domain Validation Secure Server CA
   i:/C=US/ST=New Jersey/L=Jersey City/O=The USERTRUST Network/CN=USERTrust RSA Certification Authority
 2 s:/C=US/ST=New Jersey/L=Jersey City/O=The USERTRUST Network/CN=USERTrust RSA Certification Authority
   i:/C=GB/ST=Greater Manchester/L=Salford/O=Comodo CA Limited/CN=AAA Certificate Services
---
Server certificate
-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----
subject=/CN=*.servermx.com
issuer=/C=GB/ST=Greater Manchester/L=Salford/O=Sectigo Limited/CN=Sectigo RSA Domain Validation Secure Server CA
---
No client certificate CA names sent
Peer signing digest: SHA512
Server Temp Key: ECDH, P-256, 256 bits
---
SSL handshake has read 5285 bytes and written 450 bytes
---
New, TLSv1/SSLv3, Cipher is ECDHE-RSA-AES256-GCM-SHA384
Server public key is 2048 bit
Secure Renegotiation IS supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
SSL-Session:
    Protocol  : TLSv1.2
    Cipher    : ECDHE-RSA-AES256-GCM-SHA384
    Session-ID: 2A6A75EDE3724E97BA671378962F969EA39545456F4B7A6A89A6856D659E44B9
    Session-ID-ctx: 
    Master-Key: 51D7A33F5391091E687432899F645B597D547294BE305EC759A1FAF1A86FBD45EEFEDFCEEA416F53C554DD0425054D71
    Key-Arg   : None
    Krb5 Principal: None
    PSK identity: None
    PSK identity hint: None
    Start Time: 1761702751
    Timeout   : 300 (sec)
    Verify return code: 0 (ok)
---
250 HELP
quit
221 ns11.servermx.com closing connection
closed
 
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