ERROR - MailTransportSender Error creating mail message or sending it to the configured server + wso2

Hi Friends,

If you are getting the below error, when trying to send a mail. This occurs due to a simple issue :)
I got this issue while configuring WSO2 ESB to send mails.

 ERROR - MailTransportSender Error creating mail message or sending it to the configured server  
 javax.mail.AuthenticationFailedException  
 at javax.mail.Service.connect(Service.java:306)  
 at javax.mail.Service.connect(Service.java:156)  
 at javax.mail.Service.connect(Service.java:105)  
 at javax.mail.Transport.send0(Transport.java:168)  
 at javax.mail.Transport.send(Transport.java:98)  
 at org.apache.axis2.transport.mail.MailTransportSender.sendMail(MailTransportSender.java:489)  
 at org.apache.axis2.transport.mail.MailTransportSender.sendMessage(MailTransportSender.java:175)  
 at org.apache.axis2.transport.base.AbstractTransportSender.invoke(AbstractTransportSender.java:112)  
 at org.apache.axis2.engine.AxisEngine.send(AxisEngine.java:442)  
 at org.apache.axis2.description.OutOnlyAxisOperationClient.executeImpl(OutOnlyAxisOperation.java:297)  
 at org.apache.axis2.client.OperationClient.execute(OperationClient.java:149)  
 at org.apache.synapse.core.axis2.Axis2FlexibleMEPClient.send(Axis2FlexibleMEPClient.java:482)  
 at org.apache.synapse.core.axis2.Axis2Sender.sendOn(Axis2Sender.java:59)  
 at org.apache.synapse.core.axis2.Axis2SynapseEnvironment.send(Axis2SynapseEnvironment.java:338)  
 at org.apache.synapse.endpoints.AbstractEndpoint.send(AbstractEndpoint.java:333)  
 at org.apache.synapse.endpoints.AddressEndpoint.send(AddressEndpoint.java:59)  
 at org.apache.synapse.mediators.builtin.SendMediator.mediate(SendMediator.java:97)  
 at org.apache.synapse.mediators.AbstractListMediator.mediate(AbstractListMediator.java:77)  
 at org.apache.synapse.mediators.AbstractListMediator.mediate(AbstractListMediator.java:47)  
 at org.apache.synapse.mediators.base.SequenceMediator.mediate(SequenceMediator.java:131)  
 at org.apache.synapse.mediators.MediatorFaultHandler.onFault(MediatorFaultHandler.java:85)  
 at org.apache.synapse.FaultHandler.handleFault(FaultHandler.java:54)  
 at org.apache.synapse.endpoints.AbstractEndpoint.invokeNextFaultHandler(AbstractEndpoint.java:640)  
 at org.apache.synapse.endpoints.AbstractEndpoint.onFault(AbstractEndpoint.java:475)  
 at org.apache.synapse.endpoints.AddressEndpoint.onFault(AddressEndpoint.java:43)  
 at org.apache.synapse.FaultHandler.handleFault(FaultHandler.java:102)  
 at org.apache.synapse.core.axis2.SynapseCallbackReceiver.handleMessage(SynapseCallbackReceiver.java:252)  
 at org.apache.synapse.core.axis2.SynapseCallbackReceiver.receive(SynapseCallbackReceiver.java:170)  
 at org.apache.synapse.transport.passthru.TargetErrorHandler$1.run(TargetErrorHandler.java:134)  
 at org.apache.axis2.transport.base.threads.NativeWorkerPool$1.run(NativeWorkerPool.java:172)  
 at java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1145)  
 at java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:615)  
 at java.lang.Thread.run(Thread.java:745)  
 [2015-04-20 16:28:31,370] ERROR - MailTransportSender Error generating mail message  
 org.apache.axis2.AxisFault: Error creating mail message or sending it to the configured server  
 at org.apache.axis2.transport.base.AbstractTransportSender.handleException(AbstractTransportSender.java:226)  
 at org.apache.axis2.transport.mail.MailTransportSender.sendMail(MailTransportSender.java:500)  
 at org.apache.axis2.transport.mail.MailTransportSender.sendMessage(MailTransportSender.java:175)  
 at org.apache.axis2.transport.base.AbstractTransportSender.invoke(AbstractTransportSender.java:112)  
 at org.apache.axis2.engine.AxisEngine.send(AxisEngine.java:442)  
 at org.apache.axis2.description.OutOnlyAxisOperationClient.executeImpl(OutOnlyAxisOperation.java:297)  
 at org.apache.axis2.client.OperationClient.execute(OperationClient.java:149)  
 at org.apache.synapse.core.axis2.Axis2FlexibleMEPClient.send(Axis2FlexibleMEPClient.java:482)  
 at org.apache.synapse.core.axis2.Axis2Sender.sendOn(Axis2Sender.java:59)  
 at org.apache.synapse.core.axis2.Axis2SynapseEnvironment.send(Axis2SynapseEnvironment.java:338)  
 at org.apache.synapse.endpoints.AbstractEndpoint.send(AbstractEndpoint.java:333)  
 at org.apache.synapse.endpoints.AddressEndpoint.send(AddressEndpoint.java:59)  
 at org.apache.synapse.mediators.builtin.SendMediator.mediate(SendMediator.java:97)  
 at org.apache.synapse.mediators.AbstractListMediator.mediate(AbstractListMediator.java:77)  
 at org.apache.synapse.mediators.AbstractListMediator.mediate(AbstractListMediator.java:47)  
 at org.apache.synapse.mediators.base.SequenceMediator.mediate(SequenceMediator.java:131)  
 at org.apache.synapse.mediators.MediatorFaultHandler.onFault(MediatorFaultHandler.java:85)  
 at org.apache.synapse.FaultHandler.handleFault(FaultHandler.java:54)  
 at org.apache.synapse.endpoints.AbstractEndpoint.invokeNextFaultHandler(AbstractEndpoint.java:640)  
 at org.apache.synapse.endpoints.AbstractEndpoint.onFault(AbstractEndpoint.java:475)  
 at org.apache.synapse.endpoints.AddressEndpoint.onFault(AddressEndpoint.java:43)  
 at org.apache.synapse.FaultHandler.handleFault(FaultHandler.java:102)  
 at org.apache.synapse.core.axis2.SynapseCallbackReceiver.handleMessage(SynapseCallbackReceiver.java:252)  
 at org.apache.synapse.core.axis2.SynapseCallbackReceiver.receive(SynapseCallbackReceiver.java:170)  
 at org.apache.synapse.transport.passthru.TargetErrorHandler$1.run(TargetErrorHandler.java:134)  
 at org.apache.axis2.transport.base.threads.NativeWorkerPool$1.run(NativeWorkerPool.java:172)  
 at java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1145)  
 at java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:615)  
 at java.lang.Thread.run(Thread.java:745)  
 Caused by: javax.mail.AuthenticationFailedException  
 at javax.mail.Service.connect(Service.java:306)  
 at javax.mail.Service.connect(Service.java:156)  
 at javax.mail.Service.connect(Service.java:105)  
 at javax.mail.Transport.send0(Transport.java:168)  
 at javax.mail.Transport.send(Transport.java:98)  
 at org.apache.axis2.transport.mail.MailTransportSender.sendMail(MailTransportSender.java:489)  
 ... 27 more  

First thing you should do is check if you have configure the MailTransportSender property correctly in the axis2.xml file
which is in $Carbon.Home/repository/conf/axis2/axis2.xml

   <transportSender name="mailto" class="org.apache.axis2.transport.mail.MailTransportSender">  
     <parameter name="mail.smtp.from">vinurip1@gmail.com</parameter>  
     <parameter name="mail.smtp.user">vinurip1</parameter>  
     <parameter name="mail.smtp.password">mypassword</parameter>  
     <parameter name="mail.smtp.host">smtp.gmail.com</parameter>c  
     <parameter name="mail.smtp.port">587</parameter>  
     <parameter name="mail.smtp.starttls.enable">true</parameter>  
     <parameter name="mail.smtp.auth">true</parameter>  
   </transportSender>  

If all you details are correct but still get the issue go to you mail account and check for the permission. In Gmail they send a mail saying "blocked a sign-in attempt" or similar.

If this is also not working feel free to put a comment and ask questions :)

Best Regards,
~Vinu~