Sending Email through an SMTP Server via SSL Fails Due to Resource Configuration
Symptoms
When sending a test email via an SSL connection (configured as a JNDI resource), mail won't be sent and the following error message is displayed:
javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?
Cause
The issue is caused due to the inclusion of mail.smtp.socketFactory.class property in the JNDI definition:
<Resource name="mail/SmtpServer"
auth="Container"
type="javax.mail.Session"
mail.smtp.host="mail.mycompany.com"
mail.smtp.port="587"
mail.smtp.auth="true"
mail.smtp.user="jira@mycompany.com"
password="mypassword"
mail.smtp.starttls.enable="true"
mail.smtp.socketFactory.class="javax.net.ssl.SSLSocketFactory"
/>
Resolution
Remove the mail.smtp.socketFactory.class="javax.net.ssl.SSLSocketFactory" line in conf/server.xml and restart JIRA.
Last modified on Mar 30, 2016
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