SMTP Issue After Migrate From Cloud to JIRA Server

Platform Notice: Cloud and Data Center - This article applies equally to both cloud 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

After migrating from JIRA cloud to server mails stuck in the mail queue

The following appears in the atlassian-jira-outgoing-mail.log:

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 2015-08-04 11:17:10,032 ERROR [] Sending mailitem To='xxxxx@xxxx.com' Subject='(CMS-136) test' From='jira@xxxxxx.atlassian.net' FromName='Sam Omidi (JIRA)' Cc='null' Bcc='null' ReplyTo='null' InReplyTo='<JIRA.11700.1438657574000@Atlassian.JIRA>' MimeType='text/html' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@3964f166' MessageId='null' anonymous Mail Queue Service Error occurred in sending e-mail: To='xxxxx@amristar.com' Subject='(CMS-136) test' From='jira@xxxxx.atlassian.net' FromName='Sam Omidi (JIRA)' Cc='null' Bcc='null' ReplyTo='null' InReplyTo='<JIRA.11700.1438657574000@Atlassian.JIRA>' MimeType='text/html' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@3964f166' MessageId='null' com.atlassian.mail.MailException: javax.mail.SendFailedException: Invalid Addresses; nested exception is: com.sun.mail.smtp.SMTPAddressFailedException: 550 5.7.1 Unable to relay ... ... Caused by: javax.mail.SendFailedException: Invalid Addresses; nested exception is: com.sun.mail.smtp.SMTPAddressFailedException: 550 5.7.1 Unable to relay at com.sun.mail.smtp.SMTPTransport.rcptTo(SMTPTransport.java:1873) at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1120) at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:175) ... 18 more Caused by: com.sun.mail.smtp.SMTPAddressFailedException: 550 5.7.1 Unable to relay at com.sun.mail.smtp.SMTPTransport.rcptTo(SMTPTransport.java:1724) ... 20 more  

Cause

This is because the outgoing mail configuration is still set for Cloud Outgoing mail.

By looking at the from part in the stack trace. The outgoing mail is still from JIRA Cloud.

1 From='jira@xxxxxx.atlassian.net'

Configuration needs to be done for outgoing mail according to JIRA server settings.

Resolution

Configure the outgoing mail by referring to below document:

Updated on April 8, 2025

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