Cannot send mail using SecureSMTPClientSession if SMTP server uses Post-Handshake Session Ticket #4874

exeyer · 2025-02-17T18:07:10Z

Describe the bug
Cannot send mail using SecureSMTPClientSession if SMTP server uses Post-Handshake Session Ticket. The code below works fine with GMail, it's not use session ticket.

But for many others SMTP server it's failed. For example smtp.outlook.com:

openssl s_client -connect smtp.outlook.com:587 -starttls smtp
....
250 SMTPUTF8

Post-Handshake New Session Ticket arrived:
SSL-Session:
Protocol : TLSv1.3
Cipher : TLS_AES_256_GCM_SHA384
....

To Reproduce
This code throws an exception in startTLS(): error:0A00010B:SSL routines::wrong version number
int TestEmail()
{
try
{
// Create a mail message
Poco::Net::MailMessage message;
message.setSender("[email protected]");
message.addRecipient(Poco::Net::MailRecipient(Poco::Net::MailRecipient::PRIMARY_RECIPIENT, "[email protected]"));
message.setSubject("HTML Email from Poco");

    // Set content type to HTML
    message.setContentType("text/html");

    // Provide HTML content as the message body
    message.setContent("<html><body><h1>Hello</h1><p>This is an HTML email from Poco.</p></body></html>");

    // Create an SMTP session (change the server and port accordingly)
    Poco::Net::SecureSMTPClientSession session("smtp.outlook.com", 587);
    session.setTimeout(Poco::Timespan(20, 0));
    session.open();
    std::string response;
    session.sendCommand("EHLO smtp.outlook.com\r\n", response);
    std::cout << response << std::endl;

    // Initialize the SSL manager (needed for secure connections)
    Poco::Net::initializeSSL();
    Poco::SharedPtr<Poco::Net::InvalidCertificateHandler> ptrHandler = new Poco::Net::AcceptCertificateHandler(false);
    Poco::Net::Context::Ptr ptrContext = new Poco::Net::Context(Poco::Net::Context::TLS_CLIENT_USE, "", "", "",
        Poco::Net::Context::VERIFY_NONE, 9, true, "ALL:!ADH:!LOW:!EXP:!MD5:@STRENGTH");
  
    Poco::Net::SSLManager::instance().initializeClient(NULL, ptrHandler, ptrContext);

    session.login();
    if(session.startTLS(ptrContext))
    {
        session.login(Poco::Net::SecureSMTPClientSession::AUTH_LOGIN, "[email protected]", "******");
        session.sendMessage(message);
    }

    // Close the session
    session.close();
}
catch (Poco::Net::SMTPException& e)
{
    std::cout << e.message() << std::endl;
}
catch (Poco::Net::NetException& e)
{
    std::cout << e.message() << std::endl;
}
catch (const std::exception& e)
{
    std::cout << e.what() << std::endl;
}
// Cleanup SSL manager
Poco::Net::uninitializeSSL();

return 0;

}

Expected behavior
SecureSMTPClientSession can send messages with smtp.outlook.com, smtp.yandex.com and any others with session tickets.

Logs
250-GV3P280CA0113.outlook.office365.com Hello [xxx.xxx.xxx.xxx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-8BITMIME
250-BINARYMIME
250-CHUNKING
250 SMTPUTF8
error:0A00010B:SSL routines::wrong version number

Please add relevant environment information:

Ubuntu 22.04.5 LTS
POCO 1.13.3
OpenSSL 3.0.2 15 Mar 2022

The text was updated successfully, but these errors were encountered:

exeyer added the bug label Feb 17, 2025

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Cannot send mail using SecureSMTPClientSession if SMTP server uses Post-Handshake Session Ticket #4874

Cannot send mail using SecureSMTPClientSession if SMTP server uses Post-Handshake Session Ticket #4874

exeyer commented Feb 17, 2025

Cannot send mail using SecureSMTPClientSession if SMTP server uses Post-Handshake Session Ticket #4874

Cannot send mail using SecureSMTPClientSession if SMTP server uses Post-Handshake Session Ticket #4874

Comments

exeyer commented Feb 17, 2025

openssl s_client -connect smtp.outlook.com:587 -starttls smtp .... 250 SMTPUTF8

openssl s_client -connect smtp.outlook.com:587 -starttls smtp
....
250 SMTPUTF8