Could not connect to SMTP host: smtp.office365.com, port: 587;

Question

I have configured Jenkins exactly How to configure Jenkins email Notifications through outlook?

It was working fine few days back but recently start failing. My Jenkins was Jenkins ver. 2.1, I have upgraded it to Jenkins ver. 2.33 but still no luck. here is error logs.

javax.mail.MessagingException: Could not connect to SMTP host: smtp.office365.com, port: 587;
  nested exception is:
    java.net.ConnectException: Connection timed out: connect

    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:581)

    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 org.kohsuke.stapler.Function$InstanceFunction.invoke(Function.java:335)

    at org.kohsuke.stapler.Function.bindAndInvoke(Function.java:175)

    at org.kohsuke.stapler.Function.bindAndInvokeAndServeResponse(Function.java:108)

    at org.kohsuke.stapler.MetaClass$1.doDispatch(MetaClass.java:124)

    at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:58)

    at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:746)

    at org.kohsuke.stapler.Stapler.invoke(Stapler.java:876)

    at org.kohsuke.stapler.MetaClass$5.doDispatch(MetaClass.java:236)

    at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:58)

    at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:746)

    at org.kohsuke.stapler.Stapler.invoke(Stapler.java:876)

    at org.kohsuke.stapler.Stapler.invoke(Stapler.java:649)

    at org.kohsuke.stapler.Stapler.service(Stapler.java:238)

    at javax.servlet.http.HttpServlet.service(HttpServlet.java:790)

    at org.eclipse.jetty.servlet.ServletHolder.handle(ServletHolder.java:812)

    at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1669)

    at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:135)

    at hudson.plugins.greenballs.GreenBallFilter.doFilter(GreenBallFilter.java:59)

    at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:132)

    at hudson.util.PluginServletFilter.doFilter(PluginServletFilter.java:126)

    at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652)

    at hudson.security.csrf.CrumbFilter.doFilter(CrumbFilter.java:49)

    at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652)

    at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:84)

    at hudson.security.UnwrapSecurityExceptionFilter.doFilter(UnwrapSecurityExceptionFilter.java:51)

    at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)

    at jenkins.security.ExceptionTranslationFilter.doFilter(ExceptionTranslationFilter.java:117)

    at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)

    at org.acegisecurity.providers.anonymous.AnonymousProcessingFilter.doFilter(AnonymousProcessingFilter.java:125)

    at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)

    at org.acegisecurity.ui.rememberme.RememberMeProcessingFilter.doFilter(RememberMeProcessingFilter.java:142)

    at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)

    at org.acegisecurity.ui.AbstractProcessingFilter.doFilter(AbstractProcessingFilter.java:271)

    at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)

    at jenkins.security.BasicHeaderProcessor.doFilter(BasicHeaderProcessor.java:93)

    at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)

    at org.acegisecurity.context.HttpSessionContextIntegrationFilter.doFilter(HttpSessionContextIntegrationFilter.java:249)

    at hudson.security.HttpSessionContextIntegrationFilter2.doFilter(HttpSessionContextIntegrationFilter2.java:67)

    at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)

    at hudson.security.ChainedServletFilter.doFilter(ChainedServletFilter.java:76)

    at hudson.security.HudsonFilter.doFilter(HudsonFilter.java:171)

    at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652)

    at org.kohsuke.stapler.compression.CompressionFilter.doFilter(CompressionFilter.java:49)

    at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652)

    at hudson.util.CharacterEncodingFilter.doFilter(CharacterEncodingFilter.java:82)

    at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652)

    at org.kohsuke.stapler.DiagnosticThreadNameFilter.doFilter(DiagnosticThreadNameFilter.java:30)

    at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1652)

    at org.eclipse.jetty.servlet.ServletHandler.doHandle(ServletHandler.java:585)

    at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:143)

    at org.eclipse.jetty.security.SecurityHandler.handle(SecurityHandler.java:553)

    at org.eclipse.jetty.server.session.SessionHandler.doHandle(SessionHandler.java:223)

    at org.eclipse.jetty.server.handler.ContextHandler.doHandle(ContextHandler.java:1127)

    at org.eclipse.jetty.servlet.ServletHandler.doScope(ServletHandler.java:515)

    at org.eclipse.jetty.server.session.SessionHandler.doScope(SessionHandler.java:185)

    at org.eclipse.jetty.server.handler.ContextHandler.doScope(ContextHandler.java:1061)

    at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:141)

    at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:97)

    at org.eclipse.jetty.server.Server.handle(Server.java:499)

    at org.eclipse.jetty.server.HttpChannel.handle(HttpChannel.java:311)

    at org.eclipse.jetty.server.HttpConnection.onFillable(HttpConnection.java:257)

    at org.eclipse.jetty.io.AbstractConnection$2.run(AbstractConnection.java:544)

    at winstone.BoundedExecutorService$1.run(BoundedExecutorService.java:77)

    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: java.net.ConnectException: Connection timed out: connect

    at java.net.DualStackPlainSocketImpl.waitForConnect(Native Method)

    at java.net.DualStackPlainSocketImpl.socketConnect(Unknown Source)

    at java.net.AbstractPlainSocketImpl.doConnect(Unknown Source)

    at java.net.AbstractPlainSocketImpl.connectToAddress(Unknown Source)

    at java.net.AbstractPlainSocketImpl.connect(Unknown Source)

    at java.net.PlainSocketImpl.connect(Unknown Source)

    at java.net.SocksSocketImpl.connect(Unknown Source)

    at java.net.Socket.connect(Unknown Source)

    at com.sun.mail.util.SocketFetcher.createSocket(SocketFetcher.java:286)

    at com.sun.mail.util.SocketFetcher.getSocket(SocketFetcher.java:231)

    at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:1900)

    ... 77 more

Solution 1

Actually our company changed SMTP server and blocked all open default port which wasn't allowing us to send a mail.

We got new configuration and now it's working fine.

1)  SMTP Server: ourSMTP.smtp.com
2)  Port: our_port_no.
3)  No Authentication required.
4)  SSL Unchecked.

Solution 2

Outlook SMTP need TLS... in jenkins.xml (located in installation directory) add argument

<service>
  ...
  <arguments>-Dmail.smtp.starttls.enable=true ...

select Manage Jenkins > Configure System and set:

Jenkins Location:
    System Admin e-mail address:  
         [email protected]

E-Mail Notification:
    SMTP server: smtp.office365.com

    [Under Advanced...]
    Use SMTP Authentication: checked
        User Name: [email protected]
        Password:  [ValidUser's email password]
        Use SSL:   [UNCHECKED!!]
        SMTP Port:  587

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