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POJenkins on Windows - Could not connect to SMTP host, "Unrecognized SSL message"
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  1. POJenkins on Windows - Could not connect to SMTP host, "Unrecognized SSL message"
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    copied!<p>How do I enable STARTTLS for Jenkins running on Windows?</p> <p>I have Jenkins running on a Windows 2008 server, and my email notifications are configured with the following info:</p> <ul> <li>Host: smtp.office365.com</li> <li>Port: 587</li> <li>SMTP Auth: True</li> <li>SSL: True</li> <li>etc...</li> </ul> <p>When I run a test, I get the following exception message:</p> <pre><code>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? </code></pre> <p>The issue seems to be due to <strong>smtp.office365.com</strong> using <strong>STARTTLS</strong> for the connection security. I have tried to enable <strong>STARTTLS</strong> through the <em>jenkins.xml</em> config file, by adding the following argument:</p> <p><strong>-Dmail.smtp.starttls.enable=true</strong></p> <ol> <li>Is this correct switch/parameter?</li> <li>Is <em>jenkins.xml</em> the correct file to update? </li> </ol> <p><strong>Note</strong>: I am aware, some people have solved this in their Linux environment, but I am looking for a solution that's specific to Windows. Below is a snippet of my current jenkins.xml file:</p> <pre><code>&lt;service&gt; &lt;id&gt;jenkins&lt;/id&gt; &lt;name&gt;Jenkins&lt;/name&gt; &lt;description&gt;This service runs Jenkins continuous integration system.&lt;/description&gt; &lt;env name="JENKINS_HOME" value="%BASE%"/&gt; &lt;!-- if you'd like to run Jenkins with a specific version of Java, specify a full path to java.exe. The following value assumes that you have java in your PATH. --&gt; &lt;executable&gt;%BASE%\jre\bin\java&lt;/executable&gt; &lt;arguments&gt;-Xrs -Xmx256m -Dhudson.lifecycle=hudson.lifecycle.WindowsServiceLifecycle -jar "%BASE%\jenkins.war" --httpPort=8080 -Dmail.smtp.starttls.enable=true&lt;/arguments&gt; &lt;!-- interactive flag causes the empty black Java window to be displayed. I'm still debugging this. &lt;interactive /&gt; --&gt; &lt;logmode&gt;rotate&lt;/logmode&gt; &lt;onfailure action="restart" /&gt; &lt;/service&gt; </code></pre>
 

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