Jira notification emails fail to be sent due to the "Unrecognized SSL message" error

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Platform notice: Server and Data Center only. This article only applies to Atlassian products on the Server and Data Center platforms.

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

Problem

Jira notifications emails are not and the following appears in the atlassian-jira-outgoing-mail.log file:

Caused by: javax.mail.MessagingException: Could not connect to SMTP host: smtp.gmail.com, port: 587;
nested exception is:
javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?
at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:2056) [javax.mail-1.5.4.jar:1.5.4]
at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:697) [javax.mail-1.5.4.jar:1.5.4]
at javax.mail.Service.connect(Service.java:386) [javax.mail-1.5.4.jar:1.5.4]
at javax.mail.Service.connect(Service.java:245) [javax.mail-1.5.4.jar:1.5.4]
at javax.mail.Service.connect(Service.java:194) [javax.mail-1.5.4.jar:1.5.4]
at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:174) [atlassian-mail-2.5.16.jar:?]
... 25 more

Environment

Jira Server/Data Center on any version from 8.0.0.

Cause

The configured mail server has TLS security in place, hence you would need to select this option for Jira to be able to use it for sending mails.

Resolution

Check the TLS option in the outgoing mail configuration page.

(info) Confirm with your mail server admin that what you have configured is what is expected by the mail server.


Last modified on Sep 12, 2024

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