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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Platform Notice: Data Center - This article applies to Atlassian products on the Data Center platform.

Note that this knowledge base article was created for the Data Center version of the product. Data Center knowledge base articles for non-Data Center-specific features may also work for Server versions of the product, however they have not been tested. Support for Server* products ended on February 15th 2024. If you are running a Server product, you can visit the Atlassian Server end of support announcement to review your migration options.

*Except Fisheye and Crucible

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.

Environment

Jira Server/Data Center on any version from 8.0.0.

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 12, 2024

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