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  1. Jenkins
  2. JENKINS-40431

After Jenkins Upgrade, sending email failing with error : Could not connect to SMTP host: smtp.office365.com, port: 587

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    • Icon: Bug Bug
    • Resolution: Not A Defect
    • Icon: Major Major
    • email-ext-plugin
    • None
    • Windows Server 2008 R2 Enterprise, 64 bit
      java version "1.7.0_79"
      Java(TM) SE Runtime Environment (build 1.7.0_79-b15)
      Java HotSpot(TM) 64-Bit Server VM (build 24.79-b02, mixed mode)

      Jenkins: Jenkins ver. 2.34

      Added following param in Jenkins.xml file in Jenkins root directory

      -Dmail.smtp.starttls.enable=true      # Starts TLS for Office365 SMTP Authentication
      

      Also, I unchecked

      Use SSL
      

      I have configured Jenkins email settings as

      1. SMTP server=smtp.office365.com
      2. Default user e-mail suffix=@mycompany.com
      3. Use SMTP Authentication (Checked)
      4. User Name = my-name@mycompany.com
      5. password = ********************
      
       **6. Use SSL (Un-Checked)**
      
      7. SMTP Port = 587
      8. Reply-To Address = my-name@mycompany.com
      9. Charset = UTF8
      

      And getting error for Test Configuration.

      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.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)
      
      	... 75 more
      

            davidvanlaatum David van Laatum
            swapnilvkotwal Swapnil Kotwal
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              Created:
              Updated:
              Resolved: