Sending email from Fisheye fails due to 501 Syntax: HELO hostname error
Platform Notice: Data Center Only - This article only applies to Atlassian apps on the Data Center platform.
Note that this KB was created for the Data Center version of the product. Data Center KBs 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
Getting the error below in the UI when trying to send emails from Fisheye:

The following error is logged in fisheye-mail-date.log file:
2012-05-04 14:18:16,863 ERROR [FE-WatchChecker] fisheye.mail com.cenqua.fisheye.mail.Mailer-sendMessage - problem sending email
javax.mail.MessagingException: 501 Syntax: HELO hostname
at com.sun.mail.smtp.SMTPTransport.issueCommand(SMTPTransport.java:1363)
at com.sun.mail.smtp.SMTPTransport.helo(SMTPTransport.java:838)
at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:375)
at javax.mail.Service.connect(Service.java:275)
at javax.mail.Service.connect(Service.java:156)
at javax.mail.Service.connect(Service.java:105)
at javax.mail.Transport.send0(Transport.java:168)
at javax.mail.Transport.send(Transport.java:98)
at com.cenqua.fisheye.mail.Mailer.send(Mailer.java:217)
at com.cenqua.fisheye.mail.Mailer.sendMessage(Mailer.java:193)
at com.cenqua.fisheye.web.DefaultWatchManager.sendWatchEmail(DefaultWatchManager.java:690)
at com.cenqua.fisheye.web.DefaultWatchManager.sendEmailForChangesets(DefaultWatchManager.java:611)
at com.cenqua.fisheye.web.DefaultWatchManager.access$400(DefaultWatchManager.java:63)
at com.cenqua.fisheye.web.DefaultWatchManager$WatchChecker.checkWatchesForRep(DefaultWatchManager.java:279)
at com.cenqua.fisheye.web.DefaultWatchManager$WatchChecker.checkWatchesForRep(DefaultWatchManager.java:211)
at com.cenqua.fisheye.web.DefaultWatchManager$WatchChecker.run(DefaultWatchManager.java:184)
at java.lang.Thread.run(Thread.java:662)Cause
Server's hostname is not defined, so Fisheye sends the server's IP address instead of the hostname.
Resolution
Edit /etc/hosts file adding an entry to convert your computer's IP to its hostname.
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