How to change the security type from SSL to TLS in Jenkins?

Question

I am trying to setup the smtp email notification. I could see that the gmail part works fine. I want to configure it for my office 365.

Smtp server = smtp.office365.com

We don't have SSL configured. Instead we use TLS. How can I set the TLS in the Jenkins? There is only a check button which suggests to use SSL or not. If I disable it what is it going to use?

I get the following errors -

Failed to send out e-mail  javax.mail.MessagingException: Could not connect to SMTP host: smtp.office365.com, port: 587;   nested exception is:     javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?     at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:1934)     at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:638)     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 hudson.tasks.Mailer$DescriptorImpl.doSendTestMail(Mailer.java:499)     at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)     at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:57)     at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43)     at java.lang.reflect.Method.invoke(Method.java:616)     at org.kohsuke.stapler.Function$InstanceFunction.invoke(Function.java:298)     at org.kohsuke.stapler.Function.bindAndInvoke(Function.java:161)     at org.kohsuke.stapler.Function.bindAndInvokeAndServeResponse(Function.java:96)     at org.kohsuke.stapler.MetaClass$1.doDispatch(MetaClass.java:120)     at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:53)     at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:728)     at org.kohsuke.stapler.Stapler.invoke(Stapler.java:858)     at org.kohsuke.stapler.MetaClass$6.doDispatch(MetaClass.java:248)     at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:53)     at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:728)     at org.kohsuke.stapler.Stapler.invoke(Stapler.java:858)     at org.kohsuke.stapler.Stapler.invoke(Stapler.java:631)     at org.kohsuke.stapler.Stapler.service(Stapler.java:225)     at javax.servlet.http.HttpServlet.service(HttpServlet.java:848)     at org.eclipse.jetty.servlet.ServletHolder.handle(ServletHolder.java:686)     at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1494)     at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:96)     at hudson.util.PluginServletFilter.doFilter(PluginServletFilter.java:88)     at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1482)     at hudson.security.csrf.CrumbFilter.doFilter(CrumbFilter.java:48)     at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1482)     at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:84)     at hudson.security.ChainedServletFilter.doFilter(ChainedServletFilter.java:76)     at hudson.security.HudsonFilter.doFilter(HudsonFilter.java:164)     at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1482)     at org.kohsuke.stapler.compression.CompressionFilter.doFilter(CompressionFilter.java:46)     at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1482)     at hudson.util.CharacterEncodingFilter.doFilter(CharacterEncodingFilter.java:81)     at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1474)     at org.eclipse.jetty.servlet.ServletHandler.doHandle(ServletHandler.java:499)     at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:137)     at org.eclipse.jetty.security.SecurityHandler.handle(SecurityHandler.java:533)     at org.eclipse.jetty.server.session.SessionHandler.doHandle(SessionHandler.java:231)     at org.eclipse.jetty.server.handler.ContextHandler.doHandle(ContextHandler.java:1086)     at org.eclipse.jetty.servlet.ServletHandler.doScope(ServletHandler.java:428)     at org.eclipse.jetty.server.session.SessionHandler.doScope(SessionHandler.java:193)     at org.eclipse.jetty.server.handler.ContextHandler.doScope(ContextHandler.java:1020)     at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:135)     at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:116)     at org.eclipse.jetty.server.Server.handle(Server.java:370)     at org.eclipse.jetty.server.AbstractHttpConnection.handleRequest(AbstractHttpConnection.java:489)     at org.eclipse.jetty.server.AbstractHttpConnection.content(AbstractHttpConnection.java:960)     at org.eclipse.jetty.server.AbstractHttpConnection$RequestHandler.content(AbstractHttpConnection.java:1021)     at org.eclipse.jetty.http.HttpParser.parseNext(HttpParser.java:865)     at org.eclipse.jetty.http.HttpParser.parseAvailable(HttpParser.java:240)     at org.eclipse.jetty.server.AsyncHttpConnection.handle(AsyncHttpConnection.java:82)     at org.eclipse.jetty.io.nio.SelectChannelEndPoint.handle(SelectChannelEndPoint.java:668)     at org.eclipse.jetty.io.nio.SelectChannelEndPoint$1.run(SelectChannelEndPoint.java:52)     at winstone.BoundedExecutorService$1.run(BoundedExecutorService.java:77)     at java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1146)     at java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:615)     at java.lang.Thread.run(Thread.java:679) Caused by: javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?     at sun.security.ssl.InputRecord.handleUnknownRecord(InputRecord.java:542)     at sun.security.ssl.InputRecord.read(InputRecord.java:374)     at sun.security.ssl.SSLSocketImpl.readRecord(SSLSocketImpl.java:850)     at sun.security.ssl.SSLSocketImpl.performInitialHandshake(SSLSocketImpl.java:1190)     at sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1217)     at sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1201)     at com.sun.mail.util.SocketFetcher.configureSSLSocket(SocketFetcher.java:507)     at com.sun.mail.util.SocketFetcher.getSocket(SocketFetcher.java:238)     at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:1900)     ... 63 more 

Answer 1

For Jenkins on Windows, open jenkins.xml and modify the arguments node

-Xrs -Xmx256m -Dhudson.lifecycle=hudson.lifecycle.WindowsServiceLifecycle -Dmail.smtp.starttls.enable=true -jar "%BASE%\jenkins.war" --httpPort=8080 

Answer 2

Office 365 indeed requires authenticated SMTP with TLS. The SSL option in the Jenkins configuration does not help, leave it unchecked. Instead add the following system property to the Jenkins VM:

-Dmail.smtp.starttls.enable=true 

For the standalone Jenkins put it in jenkins.xml from the installation folder and for Tomcat update the startup script or use tray icon on Windows.

Then restart jenkins and you're good to go.