I currently have Jenkins running on two separate Windows Server 2008 R2 servers as version 1.493 and 1.496. I created a new test job on each that does nothing more than try to run a non-existent batch file, triggering a build failure. On Jenkins 1.493, it sends the email via email-ext@2.25 both with Override Global Settings set and without. On Jenkins 1.496, it fails to connect to the smtp server regardless of whether Override Global Settings is set.

Here's the config for my test job:
<?xml version='1.0' encoding='UTF-8'?>
<project>
<actions/>
<description></description>
<keepDependencies>false</keepDependencies>
<properties/>
<scm class="hudson.scm.NullSCM"/>
<canRoam>true</canRoam>
<disabled>false</disabled>
<blockBuildWhenDownstreamBuilding>false</blockBuildWhenDownstreamBuilding>
<blockBuildWhenUpstreamBuilding>false</blockBuildWhenUpstreamBuilding>
<triggers class="vector"/>
<concurrentBuild>false</concurrentBuild>
<builders>
<hudson.tasks.BatchFile>
<command>C:\Jenkins\Test_Scripts\Nonexistent_Test_Script.bat</command>
</hudson.tasks.BatchFile>
</builders>
<publishers>
<hudson.plugins.emailext.ExtendedEmailPublisher plugin="email-ext@2.25">
<recipientList>richard.merr...@myreallybigcompany.com</recipientList>
<configuredTriggers>
<hudson.plugins.emailext.plugins.trigger.UnstableTrigger>
<email>
<recipientList></recipientList>
<subject>$PROJECT_DEFAULT_SUBJECT</subject>
<body>$PROJECT_DEFAULT_CONTENT</body>
<sendToDevelopers>false</sendToDevelopers>
<sendToRequester>false</sendToRequester>
<includeCulprits>false</includeCulprits>
<sendToRecipientList>true</sendToRecipientList>
<attachmentsPattern></attachmentsPattern>
<attachBuildLog>false</attachBuildLog>
<replyTo></replyTo>
</email>
</hudson.plugins.emailext.plugins.trigger.UnstableTrigger>
<hudson.plugins.emailext.plugins.trigger.FailureTrigger>
<email>
<recipientList></recipientList>
<subject>$PROJECT_DEFAULT_SUBJECT</subject>
<body>$PROJECT_DEFAULT_CONTENT</body>
<sendToDevelopers>false</sendToDevelopers>
<sendToRequester>false</sendToRequester>
<includeCulprits>false</includeCulprits>
<sendToRecipientList>true</sendToRecipientList>
<attachmentsPattern></attachmentsPattern>
<attachBuildLog>false</attachBuildLog>
<replyTo></replyTo>
</email>
</hudson.plugins.emailext.plugins.trigger.FailureTrigger>
</configuredTriggers>
<contentType>default</contentType>
<defaultSubject>test email from ROMBUILD Jenkins</defaultSubject>
<defaultContent>$DEFAULT_CONTENT</defaultContent>
<attachmentsPattern></attachmentsPattern>
<presendScript></presendScript>
<attachBuildLog>false</attachBuildLog>
<replyTo>richard.merr...@myreallybigcompany.com</replyTo>
</hudson.plugins.emailext.ExtendedEmailPublisher>
</publishers>
<buildWrappers/>
</project>

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