javax.mail.MessagingException: Could not convert socket to TLS

Question

I'm trying to connect to outlook server from my java app to send outgoing mail, but fails insatiately. getting the error below.

What's the SOLUTION ?

javax.mail.MessagingException: Could not convert socket to TLS;
nested exception is:
javax.net.ssl.SSLHandshakeException: Remote host terminated the handshake
at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1999)
at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:709)
at javax.mail.Service.connect(Service.java:386)
at javax.mail.Service.connect(Service.java:245)
at javax.mail.Service.connect(Service.java:194)
at javax.mail.Transport.send0(Transport.java:253)
at javax.mail.Transport.send(Transport.java:124)
at com.stupa.domain.EmailUtil.sendEmail(EmailUtil.java:66)
at com.stupa.domain.SendMail.sendMail(SendMail.java:48)
at com.stupa.dao.TicketSLADaoImpl.getITCDailyCallsStatusReport(TicketSLADaoImpl.java:17309)
at com.stupa.controller.SLAScheduleControlller.sendTCSITCTicketsReport(SLAScheduleControlller.java:100)
at com.stupa.domain.Task.runTCSReportTask(Task.java:119)
at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:62)
at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43)
at java.lang.reflect.Method.invoke(Method.java:498)
at org.springframework.scheduling.support.ScheduledMethodRunnable.run(ScheduledMethodRunnable.java:65)
at org.springframework.scheduling.support.DelegatingErrorHandlingRunnable.run(DelegatingErrorHandlingRunnable.java:54)
at org.springframework.scheduling.concurrent.ReschedulingRunnable.run(ReschedulingRunnable.java:81)
at java.util.concurrent.Executors$RunnableAdapter.call(Executors.java:511)
at java.util.concurrent.FutureTask.run(FutureTask.java:266)
at java.util.concurrent.ScheduledThreadPoolExecutor$ScheduledFutureTask.access$201(ScheduledThreadPoolExecutor.java:180)
at java.util.concurrent.ScheduledThreadPoolExecutor$ScheduledFutureTask.run(ScheduledThreadPoolExecutor.java:293)
at java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1149)
at java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:624)
at java.lang.Thread.run(Thread.java:748)
Caused by: javax.net.ssl.SSLHandshakeException: Remote host terminated the handshake
at sun.security.ssl.SSLSocketImpl.handleEOF(SSLSocketImpl.java:1310)
at sun.security.ssl.SSLSocketImpl.decode(SSLSocketImpl.java:1151)
at sun.security.ssl.SSLSocketImpl.readHandshakeRecord(SSLSocketImpl.java:1054)
at sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:394)
at com.sun.mail.util.SocketFetcher.configureSSLSocket(SocketFetcher.java:543)
at com.sun.mail.util.SocketFetcher.startTLS(SocketFetcher.java:480)
at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1994)
... 25 more
Caused by: java.io.EOFException: SSL peer shut down incorrectly
at sun.security.ssl.SSLSocketInputRecord.decode(SSLSocketInputRecord.java:167)
at sun.security.ssl.SSLTransport.decode(SSLTransport.java:108)
at sun.security.ssl.SSLSocketImpl.decode(SSLSocketImpl.java:1143)
... 30 more

Answer 1

Hi, i had the same problem, resolved with the following properties in my code, in runtime, and only worked putting at the code

    Properties props = new Properties();
    props.setProperty("mail.smtp.starttls.enable", "true");
    props.setProperty("mail.smtp.ssl.protocols", "TLSv1.2");

Answer 2

Similar issue is occurring in our system during last 2 weeks. Fraction of failed requests is growing each day and reached 25%. No help from Microsoft support, they do not acknowledge the problem. Very frustrating.

Answer 3

I have the same problem with openjdk 8 (131 and 302 revisions)

Answer 4

Hello,

I see this is working for some. What other Properties did you need to set? I am still receiving the following exception

Exception in thread "main" com.sun.mail.util.MailConnectException: Couldn't connect to host, port: localhost, 25; timeout -1;
nested exception is:
java.net.ConnectException: Connection refused: connect

Here the Properties I am using

Properties props;
props = new Properties();
props.put("smtp.office365.com", "587");
props.put("mail.smtp.auth", true);
props.put("mail.smtp.starttls.enable", true);
props.setProperty("mail.smtp.ssl.protocols", "TLSv1.2");

Any feedback would be appreciated and helpful. Thanks!

Answer 5

Helps when you set them properly...ughhhh :-\

    Properties props = new Properties();        
    props.put("mail.smtp.host", "smtp.office365.com");
    props.put("mail.smtp.post", "587");
    props.put("mail.smtp.auth", true);
    props.put("mail.smtp.starttls.enable", true);
    props.put("mail.smtp.ssl.protocols", "TLSv1.2");