550 5.7.1 Unable to Relay Mail From Exchange Server
Outlook is not processing outbound mail from Atlassian applications. One or more of the following appears in the logs
javax.mail.SendFailedException: Invalid Addresses; nested exception is: class com.sun.mail.smtp.SMTPAddressFailedException: 550 5.7.1 Unable to relay for email@example.com
com.atlassian.mail.MailException: com.sun.mail.smtp.SMTPSendFailedException: 550 5.7.1 Command not allowed
com.atlassian.mail.MailException: javax.mail.SendFailedException: Invalid Addresses; nested exception is: com.sun.mail.smtp.SMTPAddressFailedException: 554 5.7.1 <firstname.lastname@example.org>: Relay access denied
Caused by: com.sun.mail.smtp.SMTPSendFailedException: 550 5.7.1 Client does not have permissions to send as this sender
There is a bug in JIRA tracked as part of - JRA-31238Getting issue details... STATUS which has been verified to affect instances where the project level From address is configured to be different from the global SMTP From address in JIRA.
- Using Exchange for mail with Atlassian applications
The Exchange mail server is configured to not allow users to send mail to external domains or relay messages.
Refer to the appropriate section for either Exchange 2003 or 2007:
- Open the Exchange System Manager
- Go in Administrative Groups -> Administrative group name -> Server -> Server name -> Protocols -> SMTP
- Right click on Default SMTP Virtual Server -> properties
- Access tab -> Relay button
- Select "only the list bellow" and add your domain and\or IPs you do want to allow the relay.
- Check the "Allow all computers which successfully authenticate to relay, regardless of the list above" checkbox.
Check Microsoft's forums as well.