Unable to Send Email with SMTP Server via SSL '530 5.7.0 Must issue a STARTTLS command first' Due to 'mail.smtp.starttls.enable' Property

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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:

com.atlassian.mail.MailException: com.sun.mail.smtp.SMTPSendFailedException:
530 5.7.0 Must issue a STARTTLS command first.

Cause

In the JNDI SMTP resource configuration, mail.smtp.starttls.enable isn't turned on.

Resolution


JIRA 4.4 and earlier - Click here to expand...
  1. Double check if "JNDI Location" is specified in SMTP Server Setup
  2. Edit <JIRA_Installation_Home>/conf/server.xml (Standalone) or <Catalina_Home>/conf/server.xml (Ear/War)
  3. In the SmtpServer resource section, set mail.smtp.starttls.enable as "true" and configure mail.smtp.socketFactory.class property. A resource configuration sample is shown as below:


<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"
/>

Last modified on Sep 19, 2022

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