Bamboo SMTP unable to find valid certification path to requested target - why?

Question

I have Bamboo 4.1 installed on the same server as our JIRA 5.0.4 installation.  JIRA has had working email notifications since the beginning, and is set up for SSL connections (HTTPS redirect included).  Bamboo is set up for jira.mycompany.com:8085 and is not set up for SSL.

When I configure the SMTP settings in Bamboo, I get the following error:

The mail settings you entered were not valid. Error thrown was: javax.mail.MessagingException: Can't send command to SMTP host; nested exception is: javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target

Which confuses me because bamboo isn't using certs?

My email server is Exchange 2010.

Any ideas?

Steve Thornhill2 · Answer

Matt,

Did you ever fix this - I've found a method that does work if you still need an answer

Tiago Comasseto · Answer

Hi Matt,

Is your Exchange server configured for communication over SSL? If yes, then you'll need to import Exchange's certificate into the cacerts file of the Java installation that Bamboo is using. You can see more details on how check this here.

This is the example of the import command:

keytool -import -keystore ./jre/lib/security/cacerts -file server-certificate.crt

Also, after this, you can test if the connection over SSL is right using SSLPoke, as this example:

java -Djavax.net.ssl.trustStore=/opt/java/jre/lib/security/cacerts SSLPoke smtp.gmail.com 465

Once you have the certificate imported, you can restart your Bamboo instance and attempt to configure the SMTP server again.

I hope this helps.

Cheers