Java Mail Messaging Exception

Question

So I've just begun working with the JavaMail API. I've used it in a few places in my web application (I'm using Struts2 & Hibernate) and the code for sending the email works in some places and doesn't in some places. The places it doesn't, I get a MessagingException : Could not convert socket to TLS

Here's my code. In the classes, I've defined this static block:

static Properties properties = new Properties(); static {

    properties.put("mail.smtp.starttls.enable", "true"); 
    properties.put("mail.smtp.host", "smtp.gmail.com");
    properties.put("mail.smtp.user", "usrname@domain.com"); // User name
    properties.put("mail.smtp.password", "<the_correct_password>"); // password
    properties.put("mail.smtp.port", "587");
    properties.put("mail.smtp.auth", "true");
}

And here's the code for sending the email which is within a function:

    javax.mail.Session emailSession = javax.mail.Session.getDefaultInstance(properties, 
                                    new javax.mail.Authenticator() {
                                protected PasswordAuthentication
                                getPasswordAuthentication() {
                                return new
                                PasswordAuthentication("username@domain.com", "<the_correct_password>");
                                }});

   Message message = new MimeMessage(emailSession);
   message.setFrom(new InternetAddress("usrname@domain.com"));
   message.setRecipients(Message.RecipientType.TO,InternetAddress.parse(getModel().getEmail()));
 message.setSubject("Password change!");
 message.setText("Hi "+getModel().getName()+"\n"+ "Security code - "+sb.toString());
 Transport.send(message);

Here is the exception StackTrace:

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: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 com.proconsulto.action.LoginAction.checkEmail(LoginAction.java:295)
    at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
    at sun.reflect.NativeMethodAccessorImpl.invoke(Unknown Source)
    at sun.reflect.DelegatingMethodAccessorImpl.invoke(Unknown Source)
    at java.lang.reflect.Method.invoke(Unknown Source)
    at com.opensymphony.xwork2.DefaultActionInvocation.invokeAction(DefaultActionInvocation.java:450)
    at com.opensymphony.xwork2.DefaultActionInvocation.invokeActionOnly(DefaultActionInvocation.java:289)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:252)
    at org.apache.struts2.interceptor.debugging.DebuggingInterceptor.intercept(DebuggingInterceptor.java:256)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at com.opensymphony.xwork2.interceptor.DefaultWorkflowInterceptor.doIntercept(DefaultWorkflowInterceptor.java:176)
    at com.opensymphony.xwork2.interceptor.MethodFilterInterceptor.intercept(MethodFilterInterceptor.java:98)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at com.opensymphony.xwork2.validator.ValidationInterceptor.doIntercept(ValidationInterceptor.java:265)
    at org.apache.struts2.interceptor.validation.AnnotationValidationInterceptor.doIntercept(AnnotationValidationInterceptor.java:68)
    at com.opensymphony.xwork2.interceptor.MethodFilterInterceptor.intercept(MethodFilterInterceptor.java:98)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at com.opensymphony.xwork2.interceptor.ConversionErrorInterceptor.intercept(ConversionErrorInterceptor.java:138)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at com.opensymphony.xwork2.interceptor.ParametersInterceptor.doIntercept(ParametersInterceptor.java:249)
    at com.opensymphony.xwork2.interceptor.MethodFilterInterceptor.intercept(MethodFilterInterceptor.java:98)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at com.opensymphony.xwork2.interceptor.ParametersInterceptor.doIntercept(ParametersInterceptor.java:249)
    at com.opensymphony.xwork2.interceptor.MethodFilterInterceptor.intercept(MethodFilterInterceptor.java:98)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at com.opensymphony.xwork2.interceptor.StaticParametersInterceptor.intercept(StaticParametersInterceptor.java:191)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at org.apache.struts2.interceptor.MultiselectInterceptor.intercept(MultiselectInterceptor.java:73)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at org.apache.struts2.interceptor.CheckboxInterceptor.intercept(CheckboxInterceptor.java:91)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at org.apache.struts2.interceptor.FileUploadInterceptor.intercept(FileUploadInterceptor.java:252)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at com.opensymphony.xwork2.interceptor.ModelDrivenInterceptor.intercept(ModelDrivenInterceptor.java:100)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at com.opensymphony.xwork2.interceptor.ScopedModelDrivenInterceptor.intercept(ScopedModelDrivenInterceptor.java:141)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at com.opensymphony.xwork2.interceptor.ChainingInterceptor.intercept(ChainingInterceptor.java:145)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at com.opensymphony.xwork2.interceptor.PrepareInterceptor.doIntercept(PrepareInterceptor.java:171)
    at com.opensymphony.xwork2.interceptor.MethodFilterInterceptor.intercept(MethodFilterInterceptor.java:98)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at com.opensymphony.xwork2.interceptor.I18nInterceptor.intercept(I18nInterceptor.java:176)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at org.apache.struts2.interceptor.ServletConfigInterceptor.intercept(ServletConfigInterceptor.java:164)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at com.opensymphony.xwork2.interceptor.AliasInterceptor.intercept(AliasInterceptor.java:193)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at com.opensymphony.xwork2.interceptor.ExceptionMappingInterceptor.intercept(ExceptionMappingInterceptor.java:187)
    at com.opensymphony.xwork2.DefaultActionInvocation.invoke(DefaultActionInvocation.java:246)
    at org.apache.struts2.impl.StrutsActionProxy.execute(StrutsActionProxy.java:54)
    at org.apache.struts2.dispatcher.Dispatcher.serviceAction(Dispatcher.java:546)
    at org.apache.struts2.dispatcher.ng.ExecuteOperations.executeAction(ExecuteOperations.java:77)
    at org.apache.struts2.dispatcher.ng.filter.StrutsPrepareAndExecuteFilter.doFilter(StrutsPrepareAndExecuteFilter.java:91)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:243)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:210)
    at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:224)
    at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:169)
    at org.apache.catalina.authenticator.AuthenticatorBase.invoke(AuthenticatorBase.java:472)
    at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:168)
    at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:100)
    at org.apache.catalina.valves.AccessLogValve.invoke(AccessLogValve.java:929)
    at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:118)
    at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:405)
    at org.apache.coyote.http11.AbstractHttp11Processor.process(AbstractHttp11Processor.java:964)
    at org.apache.coyote.AbstractProtocol$AbstractConnectionHandler.process(AbstractProtocol.java:515)
    at org.apache.tomcat.util.net.JIoEndpoint$SocketProcessor.run(JIoEndpoint.java:304)
    at java.util.concurrent.ThreadPoolExecutor.runWorker(Unknown Source)
    at java.util.concurrent.ThreadPoolExecutor$Worker.run(Unknown Source)
    at java.lang.Thread.run(Unknown Source)
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 sun.security.ssl.Alerts.getSSLException(Unknown Source)
    at sun.security.ssl.SSLSocketImpl.fatal(Unknown Source)
    at sun.security.ssl.Handshaker.fatalSE(Unknown Source)
    at sun.security.ssl.Handshaker.fatalSE(Unknown Source)
    at sun.security.ssl.ClientHandshaker.serverCertificate(Unknown Source)
    at sun.security.ssl.ClientHandshaker.processMessage(Unknown Source)
    at sun.security.ssl.Handshaker.processLoop(Unknown Source)
    at sun.security.ssl.Handshaker.process_record(Unknown Source)
    at sun.security.ssl.SSLSocketImpl.readRecord(Unknown Source)
    at sun.security.ssl.SSLSocketImpl.performInitialHandshake(Unknown Source)
    at sun.security.ssl.SSLSocketImpl.startHandshake(Unknown Source)
    at sun.security.ssl.SSLSocketImpl.startHandshake(Unknown Source)
    at com.sun.mail.util.SocketFetcher.configureSSLSocket(SocketFetcher.java:549)
    at com.sun.mail.util.SocketFetcher.startTLS(SocketFetcher.java:486)
    at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1902)
    ... 76 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(Unknown Source)
    at sun.security.validator.PKIXValidator.engineValidate(Unknown Source)
    at sun.security.validator.Validator.validate(Unknown Source)
    at sun.security.ssl.X509TrustManagerImpl.validate(Unknown Source)
    at sun.security.ssl.X509TrustManagerImpl.checkTrusted(Unknown Source)
    at sun.security.ssl.X509TrustManagerImpl.checkServerTrusted(Unknown Source)
    ... 87 more
Caused by: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
    at sun.security.provider.certpath.SunCertPathBuilder.engineBuild(Unknown Source)
    at java.security.cert.CertPathBuilder.build(Unknown Source)
    ... 93 more

Line 295 that's mentioned is this line : Transport.send(message)

What's surprising is, this code fails for in a few functions & works in a few of them. I've substituted the exact code dozens of times but I still can't figure out what's wrong. I thought perhaps it's not receiving the recipient address or maybe the properties are incorrect but I've doubled checked and I'm unable to understand what's causing this behaviour. Please help me!

Answer 1

I had to add another property in my static block and that worked for me:

props.put("mail.smtp.ssl.trust", "smtp.gmail.com");

Answer 2

Please refer to http://www.oracle.com/technetwork/java/javamail/faq/index.html#installcert which states:

Q: When connecting to my mail server over SSL I get an exception like "unable to find valid certification path to requested target".

A: Your server is probably using a test certificate or self-signed certificate instead of a certificate signed by a commercial Certificate Authority. You'll need to install the server's certificate into your trust store. The InstallCert program will help.

Alternatively, you can set the "mail.protocol.ssl.trust" property to the host name of your mail server. See the javadocs for the protocol provider packages for details.

Other common causes of this problem are:

• There's a firewall or anti-virus program intercepting your request.
• There's something wrong in your JDK installation preventing it from finding the certificates for the trusted certificate authorities.
• You're running in an application server that has overridden the JDK's list of trusted certificate authorities.

As you're connecting to Gmail which should have all the needed certificates present in the default truststore, the cause could likely be an anti-virus blocking your SMTP calls.