Unable to send an email using SMTP (Getting javax.mail.MessagingException: Could not convert socket to TLS;)

Question

I have written the following code for sending email using javamail API through SMTP as TLS as SSL is not supported but I ended up with the following exception. Please see my code below. I have used debugging mode and below the code you can find the exception as well.

import java.util.Properties;
import javax.mail.Message;
import javax.mail.MessagingException;
import javax.mail.PasswordAuthentication;
import javax.mail.Session;
import javax.mail.Transport;
import javax.mail.internet.InternetAddress;
import javax.mail.internet.MimeMessage;

public class SendMailTLS {

    public static void main(String[] args) {

        final String username = "[email protected]";
        final String password = "***********";

        Properties props = new Properties();
        props.put("mail.smtp.auth", "true");
        props.put("mail.smtp.starttls.enable", "true");
        props.put("mail.smtp.host", "mail.mydomain.com");
        props.put("mail.smtp.debug", "true");
        props.put("mail.smtp.port", "587");

        Session session = Session.getInstance(props,
          new javax.mail.Authenticator() {
            protected PasswordAuthentication getPasswordAuthentication() {
                return new PasswordAuthentication(username, password);
            }
          });
        session.setDebug(true);

        try {

            Message message = new MimeMessage(session);
            message.setFrom(new 
                  InternetAddress("[email protected]"));
            message.setRecipients(Message.RecipientType.TO,
            InternetAddress.parse("[email protected]"));
            message.setSubject("Testing Subject");
            message.setText("Dear Mail Crawler,"
                + "\n\n No spam to my email, please!");

            Transport.send(message);

            System.out.println("Done");

        } catch (MessagingException e) {
            throw new RuntimeException(e);
        }
    }
}

Exception trace

DEBUG: setDebug: JavaMail version 1.4.5
DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc]
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "mail.mydomain.com", port 587, isSSL false
220-cpanel35.per.syra.net.au ESMTP Exim 4.80 #2 Fri, 05 Oct 2012 17:28:56 +0800 
220-We do not authorize the use of this system to transport unsolicited, 
220 and/or bulk e-mail.
DEBUG SMTP: connected to host "mail.mydomain.com", port: 587

EHLO xxxxxx.xxxxx.com
250-cpanel35.per.syra.net.au Hello xxxx.xxxxx.com [xx.xx.xx.xxx]i
250-SIZE 52428800
250-8BITMIME
250-PIPELINING
250-AUTH PLAIN LOGIN
250-STARTTLS
250 HELP
DEBUG SMTP: Found extension "SIZE", arg "52428800"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "PIPELINING", arg ""
DEBUG SMTP: Found extension "AUTH", arg "PLAIN LOGIN"
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "HELP", arg ""
STARTTLS
220 TLS go ahead
Exception in thread "main" java.lang.RuntimeException: javax.mail.MessagingException: Could not convert socket to TLS;
  nested exception is:
    javax.net.ssl.SSLException: java.lang.RuntimeException: Could not generate DH keypair
    at SendMailTLS.main(SendMailTLS.java:52)
Caused by: javax.mail.MessagingException: Could not convert socket to TLS;
  nested exception is:
    javax.net.ssl.SSLException: java.lang.RuntimeException: Could not generate DH keypair
    at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1918)
    at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:652)
    at javax.mail.Service.connect(Service.java:317)
    at javax.mail.Service.connect(Service.java:176)
    at javax.mail.Service.connect(Service.java:125)
    at javax.mail.Transport.send0(Transport.java:194)
    at javax.mail.Transport.send(Transport.java:124)
    at SendMailTLS.main(SendMailTLS.java:47)
Caused by: javax.net.ssl.SSLException: java.lang.RuntimeException: Could not generate DH keypair
    at sun.security.ssl.Alerts.getSSLException(Alerts.java:208)
    at sun.security.ssl.SSLSocketImpl.fatal(SSLSocketImpl.java:1868)
    at sun.security.ssl.SSLSocketImpl.fatal(SSLSocketImpl.java:1826)
    at sun.security.ssl.SSLSocketImpl.handleException(SSLSocketImpl.java:1809)
    at sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1328)
    at sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1305)
    at com.sun.mail.util.SocketFetcher.configureSSLSocket(SocketFetcher.java:548)
    at com.sun.mail.util.SocketFetcher.startTLS(SocketFetcher.java:485)
    at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1913)
    ... 7 more
Caused by: java.lang.RuntimeException: Could not generate DH keypair
    at sun.security.ssl.DHCrypt.<init>(DHCrypt.java:123)
    at sun.security.ssl.ClientHandshaker.serverKeyExchange(ClientHandshaker.java:618)
    at sun.security.ssl.ClientHandshaker.processMessage(ClientHandshaker.java:202)
    at sun.security.ssl.Handshaker.processLoop(Handshaker.java:868)
    at sun.security.ssl.Handshaker.process_record(Handshaker.java:804)
    at sun.security.ssl.SSLSocketImpl.readRecord(SSLSocketImpl.java:998)
    at sun.security.ssl.SSLSocketImpl.performInitialHandshake(SSLSocketImpl.java:1294)
    at sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1321)
    ... 11 more
Caused by: java.security.InvalidAlgorithmParameterException: Prime size must be multiple of 64, and can only range from 512 to 1024 (inclusive)
    at com.sun.crypto.provider.DHKeyPairGenerator.initialize(DHKeyPairGenerator.java:120)
    at java.security.KeyPairGenerator$Delegate.initialize(KeyPairGenerator.java:658)
    at sun.security.ssl.DHCrypt.<init>(DHCrypt.java:117)
    ... 18 more

Can anyone help me debug this? Thanks in advance!

Answer 1

Commenting-out the property mail.smtp.starttls.enable means you fall back to a default and unsecured connection, which would work only if the remote SMTP host also accepts unsecured transport on port 587 (the port for mail submission versus port 25 for end-delivery or relay operations).

In my context, TLS is compulsory on 587 and any attempt to open a session without TLS yield the SMTP server error response 530 Must issue a STARTTLS command first.

Then setting mail.smtp.starttls.enable to true alone still yield the same error Could not convert socket to TLS but now with a clue: Server is not trusted. Indeed, you must have either a keystore defined in the JVM start properties that would contain a certificate chain ending onto a trusted root certificate, either enforce trust with this extra property: mail.smtp.ssl.trust set to the remote host name.

Configuring the whole stuff in Spring support for javamail for instance (which you can easily map to plain javamail API) requires all of the following:

<bean id="mailSender" class="org.springframework.mail.javamail.JavaMailSenderImpl">
<property name="host" value="theRemoteSmtpServer" />
<property name="port" value="587" />
<property name="username" value="muUserID" />
<property name="password" value="myPassword" />
<property name="javaMailProperties">
    <props>
        <prop key="mail.smtp.starttls.enable">true</prop>
        <prop key="mail.smtp.ssl.trust">theRemoteSmtpServer</prop>
        <prop key="mail.smtp.auth">true</prop>
    </props>
</property>
</bean>

Answer 2

I resolved this issue by just commenting out the below property

props.put("mail.smtp.starttls.enable", "true"); 

and the code got executed with no errors or warning or simply delete this line from the above source code. It is working like a charm till date.