jira email not working with self signed certificates?

[IT Admin]

Hi, I am using an openssl certificate and have successfully made my web server ssl by adjusting server.xml. However, when I test ending email application, it always throws an error like sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target and javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path building failed.

Should I buy a ssl certified by a trusted root authority to use jira email?

[Andy Heinzer · Accepted solution]

I'm confused here.  I don't understand what role a self signed certificate is going to play in the ability for Jira to connect to gmail.   If you're trying to connect to a secure pop or secure imap to a gmail site, then you need to make sure that you have imported the SSL certificate for that site (presumably smtp.gmail.com ) into your trust store for Jira.

I'm sure Google won't be using a self signed cert for this site.

The only way I would expect a self signed cert to be used with Jira is if you are trying to access your Jira site over SSL and you have not used a signing authority, but in this case, that shouldn't matter.

If you have already imported this, but still see this 'PKIX path building error', then the most likely answer is that you have not imported this certificate into the correct directory.   In cases like this I like to recommend that users download the current Oracle Java 8 JDK and follow the steps in Installing Java in order to set a JAVA_HOME variable on the system.  Using this method ensures that the next time Jira starts up it is using that Java JVM and in turn is using the truststore located under that specific root path.

[IT Admin]

Hi, I have installed jira and confluence on Ubuntu and Windows. On Ubuntu, the emailing function worked fine, but on Windows, it threw the error and I couldn't find any answers when goolgling. As you instructed, I have imported smtp.gmail.com with a port number of 465 into Portecle. Now everything works fine. Thank you.

[Fred]

Does anyone know how to install a self-signed certificate on Jira on CentOS without GUI?

[Shannon S]

Hi Ascan,

Please have a look at this article, which tells you how to resolve the issue you're having:

• Unable to Connect to SSL Services due to PKIX Path Building Failed

Let us know if you have any trouble.

Regards,

Shannon

[IT Admin]

SSL poking works fine, and I can connect to the web server, but only the emailing makes me crazy ~ ~... I have used Portecle by following your guidelines.

[IT Admin]

/secure/admin/VerifySmtpServerConnection!update.jspa [c.a.j.p.mail.webwork.VerifyMailServer] Unable to connect to the server at smtp.gmail.com due to the following exception: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target

my log says that...

[Shannon S]

Ascan,

 If you imported all of the certificates properly it may be an issue with the settings you're using. I would double-check that you've completed all steps in the article I sent you earlier.

Can you also let us know what settings you're using when you try to connect to Gmail? There's no need to show us your username/password, just what settings you've selected and port numbers in your SMTP setup.

Regards,

Shannon