9

I refered this doc and have configured MS 365 as follows but it throws exceptions. I have tried it with 465 port but still it's failing and also without checking Use SSL

enter image description here

but it throws this exception

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:514)

    at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)

    at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:39)

    at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25)

    at java.lang.reflect.Method.invoke(Method.java:597)

    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:121)

    at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:53)

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

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

    at org.kohsuke.stapler.MetaClass$6.doDispatch(MetaClass.java:249)

    at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:53)

    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: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:123)

    at hudson.plugins.greenballs.GreenBallFilter.doFilter(GreenBallFilter.java:58)

    at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:120)

    at hudson.util.PluginServletFilter.doFilter(PluginServletFilter.java:114)

    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.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:164)

    at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1482)

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

    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:1482)

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

    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$Worker.runTask(ThreadPoolExecutor.java:886)

    at java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:908)

    at java.lang.Thread.run(Thread.java:619)

Caused by: javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?

    at com.sun.net.ssl.internal.ssl.InputRecord.handleUnknownRecord(InputRecord.java:523)

    at com.sun.net.ssl.internal.ssl.InputRecord.read(InputRecord.java:355)

    at com.sun.net.ssl.internal.ssl.SSLSocketImpl.readRecord(SSLSocketImpl.java:789)

    at com.sun.net.ssl.internal.ssl.SSLSocketImpl.performInitialHandshake(SSLSocketImpl.java:1112)

    at com.sun.net.ssl.internal.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1139)

    at com.sun.net.ssl.internal.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1123)

    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)

    ... 82 more

3 Answers 3

6

You need to add this java argument to the Jenkins command line:

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

To do this, you have to find the script that kicks off Jenkins at system startup. On a Mac, with standard Jenkins installation, it would be in "/Library/Application Support/Jenkins/jenkins-runner.sh"

And looks something like this:

#!/bin/bash
#
# Startup script used by Jenkins launchd job.
# Mac OS X launchd process calls this script to customize
# the java process command line used to run Jenkins.
#
# Customizable parameters are found in
# /Library/Preferences/org.jenkins-ci.plist
#
# You can manipulate it using the "defaults" utility.
# See "man defaults" for details.

defaults="defaults read /Library/Preferences/org.jenkins-ci"

war=`$defaults war` || war="/Applications/Jenkins/jenkins.war"

javaArgs="-Dfile.encoding=UTF-8"
javaArgs="$javaArgs -Djava.awt.headless=true"
javaArgs="$javaArgs -Dmail.smtp.starttls.enable=true"
javaArgs="$javaArgs  -Dorg.apache.commons.jelly.tags.fmt.timeZone=America/Vancouver"
javaArgs="$javaArgs -Dhudson.DNSMultiCast.disabled=true"
...
5
  • Hi @jpadams I have added JAVA argument in my Jenkins.xml file but still the same problem persist <executable>java</executable> <arguments>-Xrs -Xmx256m -Dhudson.lifecycle=hudson.lifecycle.WindowsServiceLifecycle -jar "%BASE%\jenkins.war" --httpPort=8080 -Dmail.smtp.starttls.enable=true</arguments> Please let me know if you have any solution Feb 21, 2015 at 13:37
  • Note :- I have restarted Jenkins but problem not yet solved :( Feb 22, 2015 at 4:22
  • On 465 Port i got connection timeout javax.mail.MessagingException: Could not connect to SMTP host: smtp.office365.com, port: 465; nested exception is: java.net.ConnectException: Connection timed out: connect Feb 22, 2015 at 5:24
  • Java arguments need to come before the -jar parameter: java -Xrs -Xmx256m -Dmail.smtp.starttls.enable=true -Dhudson.lifecycle=hudson.lifecycle.WindowsServiceLifecycle -jar "%BASE%\jenkins.war" --httpPort=8080
    – jpadams
    Feb 23, 2015 at 7:16
  • No better luck using this too :( Note :- My Jenkins running on port 8181. Is it a reason for it ? <arguments>-Xrs -Xmx256m -Dmail.smtp.starttls.enable=true -Dhudson.lifecycle=hudson.lifecycle.WindowsServiceLifecycle -jar "%BASE%\jenkins.war" --httpPort=8181</arguments> Feb 23, 2015 at 7:36
5

Finally I could figure out the problem. I have missed

Default user e-mail suffix =  @mycompany.com

Also, I unchecked

Use SSL

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

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

These are my final changes

1. SMTP server=smtp.office365.com
2. Default user e-mail [email protected]
3. Use SMTP Authentication (Checked)
4. User Name = [email protected]
5. password = ********************

 **6. Use SSL (Un-Checked)**

7. SMTP Port = 587
8. Reply-To Address = [email protected]
9. Charset = UTF8

Here is Screen Shot

BOOOM ... !!!

2
  • As a side note, remember to set the System Admin e-mail address to the same one as the username of the email notification. This answer helped
    – Fabio
    Jan 12, 2018 at 10:31
  • I tried the way you have given. But not able to solve the issue. Do I need to restart any service? In my case I am running jenkins blue ocean inside my container. I posted related question here- stackoverflow.com/questions/52077290/… Aug 30, 2018 at 9:03
2

to start jenkins from war file use

java -Dmail.smtp.starttls.enable="true" -jar jenkins.war --httpPort=9090

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