Jira outgoing mail "relay access denied"

[Rob Byrd]

System:

server-hosted jira install on internal network with Linux postgres postfix et al

postfix connected via relay host to organization's "real mail server" via port 25

     edited jira host Linux /etc/postfix/mail.cf file Relayhost var to proper IP address

     Linux command line mail application properly sends mail to external address

jira will send mail to user x on the jira server, but not when recipient has external address

So it seems there may be a config item in jira I am missing. Any suggestions appreciated.

log for successful message is about 60 lines:

"Your test message has been sent successfully to [some-user@host.my-company.local]"

log for failed message is about 19 pages:

An error has occurred with sending the test email:
com.atlassian.mail.MailException: javax.mail.SendFailedException: Invalid Addresses;
nested exception is:
com.sun.mail.smtp.SMTPAddressFailedException: 454 4.7.1 <my.name@domain.com>: Relay access denied

[Rob Byrd · Accepted solution]

That was it. Changing the relay host for Apache2 web server, of course, did noting for the Tomcat server. once I changed the relay SMTP host for Tomcat via Jira System config, everything worked fine. Thank you Thomas for holding the flashlight. Couldn't have done it without that.

Rob

[Thomas Deiler]

Nice to be your flashlight, but I felt a little bit drained. ;)

[Thomas Deiler]

Dear @Rob Byrd,

on the first view, it doesn't look like a Jira issue. The reason will be grounded in your network infrastructure to block mails to non internal email addresses. Most times these are company security restrictions.

Try to send a mail from the servers' command line to an external email address to verify my theory.

echo "This is a mail body" | mailx -s "Subject" user@mail.com

So long

Thomas

[Rob Byrd]

Thomas,

First of all, thank you for working with me on this.

Yes, I should have been more clear; postfix [on the jira server] connected to the organization's real mail server and successfully sends mail from the command line.   (And I just now confirmed that again.)

So the disconnect/config issue seems to be somewhere between jira application and its Linux host.  That's why I thought there may be a config setting in jira. Since I installed jira as a service, rather than an app, jira should already have elevated privileges. Do I need to open a port other than 25? for mail. 

Rob

[Rob Byrd]

So, I did set the relay hot to a non-localhost for my organization's real email server, but that was in Apache (/etc/postfix/main.cf   relayhost = [the correct IP addr )]. And that's why the command line mail properly sends to external email address. But that is not the same as Apache Tomcat (Catalina). Where can I find the repay host config var in Catalina (which was installed by the jira application installer)?

[Thomas Deiler]

Dear @Rob Byrd,

if you could send a mail from command line to external user, the whole email chain seems to be proper configured.

Eventually a local firewall rule prevents Jira to connect to postfix. But at all you confirmed that sending mails in general works from Jira to internal. So an external mail uses the same ports as the internal mails, either you have configured your mail relay to communicate with a different server depending on the recipient.

Please activate a higher log level for the mailer class in Admin>System>Logging and Profiling. Repeat your test with an internal and an external recipient and compare.

So long

Thomas

[Thomas Deiler]

Dear @Rob Byrd,

afaik there is no mail relay host default configuration. I have never used the installer and configured the mail server within Jira. Have you been asked to enter one during the installation?

So long

Thomas

[Rob Byrd]

So in outgoing mail tab I edited the smtp host to be the relay host ip. In other words, it looks like Jira/Tomcat don't need the local host smtp service. By using the relay host directly as the smtp host the mail sent fine to an external address. ( was making it too difficult).

In Apache2 web server, I had to have the mail localhost smtp and then add the relay host in /etc/postfix/main.cf.