Sending Mail using Java Mail error

Question

I am sending a email using this code

 public static void main(String[] args) {

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

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

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

            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. hello");

                Transport.send(message);

                System.out.println("Done");

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

And then this returned me a nested exception. the stacktrace is so huge I have no idea where to start looking or how to debug this

Exception in thread "main" java.lang.RuntimeException: javax.mail.MessagingException: Could not convert socket to TLS;
  nested exception is:
    javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
    at Test.main(Test.java:44)
Caused by: javax.mail.MessagingException: Could not convert socket to TLS;
  nested exception is:
    javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
    at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1907)
    at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:666)
    at javax.mail.Service.connect(Service.java:367)
    at javax.mail.Service.connect(Service.java:226)
    at javax.mail.Service.connect(Service.java:175)
    at javax.mail.Transport.send0(Transport.java:253)
    at javax.mail.Transport.send(Transport.java:124)
    at Test.main(Test.java:39)
Caused by: javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
    at com.sun.net.ssl.internal.ssl.Alerts.getSSLException(Alerts.java:174)
    at com.sun.net.ssl.internal.ssl.SSLSocketImpl.fatal(SSLSocketImpl.java:1649)
    at com.sun.net.ssl.internal.ssl.Handshaker.fatalSE(Handshaker.java:241)
    at com.sun.net.ssl.internal.ssl.Handshaker.fatalSE(Handshaker.java:235)
    at com.sun.net.ssl.internal.ssl.ClientHandshaker.serverCertificate(ClientHandshaker.java:1206)
    at com.sun.net.ssl.internal.ssl.ClientHandshaker.processMessage(ClientHandshaker.java:136)
    at com.sun.net.ssl.internal.ssl.Handshaker.processLoop(Handshaker.java:593)
    at com.sun.net.ssl.internal.ssl.Handshaker.process_record(Handshaker.java:529)
    at com.sun.net.ssl.internal.ssl.SSLSocketImpl.readRecord(SSLSocketImpl.java:893)
    at com.sun.net.ssl.internal.ssl.SSLSocketImpl.performInitialHandshake(SSLSocketImpl.java:1138)
    at com.sun.net.ssl.internal.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1165)
    at com.sun.net.ssl.internal.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1149)
    at com.sun.mail.util.SocketFetcher.configureSSLSocket(SocketFetcher.java:528)
    at com.sun.mail.util.SocketFetcher.startTLS(SocketFetcher.java:465)
    at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1902)
    ... 7 more
Caused by: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
    at sun.security.validator.PKIXValidator.doBuild(PKIXValidator.java:323)
    at sun.security.validator.PKIXValidator.engineValidate(PKIXValidator.java:217)
    at sun.security.validator.Validator.validate(Validator.java:218)
    at com.sun.net.ssl.internal.ssl.X509TrustManagerImpl.validate(X509TrustManagerImpl.java:126)
    at com.sun.net.ssl.internal.ssl.X509TrustManagerImpl.checkServerTrusted(X509TrustManagerImpl.java:209)
    at com.sun.net.ssl.internal.ssl.X509TrustManagerImpl.checkServerTrusted(X509TrustManagerImpl.java:249)
    at com.sun.net.ssl.internal.ssl.ClientHandshaker.serverCertificate(ClientHandshaker.java:1185)
    ... 17 more
Caused by: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
    at sun.security.provider.certpath.SunCertPathBuilder.engineBuild(SunCertPathBuilder.java:174)
    at java.security.cert.CertPathBuilder.build(CertPathBuilder.java:238)
    at sun.security.validator.PKIXValidator.doBuild(PKIXValidator.java:318)
    ... 23 more

may be duplicate of stackoverflow.com/questions/16040070/… — NullPointerException
– NullPointerException, Commented Apr 19, 2013 at 15:46

Christian Bongiorno · Accepted Answer · 2013-04-19 16:47:10Z

1

Caused by: javax.mail.MessagingException: Could not convert socket to TLS;
  nested exception is:

Your SMTP server is insisting on TLS (Transport Layer Security) for encrypted sending and can't validate the server certificate.

answered Apr 19, 2013 at 16:47

Christian Bongiorno

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1 Comment

Christian Bongiorno Over a year ago

There is a JVM "-D" property you can set to ignore invalid certs (I think it includes self-signed certs which is the most common cause). I have given guidance on this I am sure you can track down the flags

user2284545 · Accepted Answer · 2013-04-20 01:11:40Z

1

Please define the properties as (using an alternative to TLS) :

Properties props = new Properties();
props.put("mail.smtp.host", "smtp.gmail.com");
props.put("mail.smtp.socketFactory.port", "465");
props.put("mail.smtp.socketFactory.class", "javax.net.ssl.SSLSocketFactory");
props.put("mail.smtp.auth", "true");
props.put("mail.smtp.port", "465");

....

See if this works.

answered Apr 20, 2013 at 1:11

user2284545

2 Comments

user962206 Over a year ago

I tied that, but it shows nothing, no exceptions. I am guessing I am having a connection timeout?

user2284545 Over a year ago

Add System.out.println() statements in various parts of your code to see where the code execution 'appears' to stop. Use try-catch blocks with the catch block having a printStackTrace() call on the Exception instance. try {} catch (Exception e) { e.printStackTrace(); }

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