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i have imported my custom certificate with intermediate certificate into my truststore which is set by: -Djavax.net.ssl.trustStore=/var/lib/bamboo/cacerts
/usr/lib/jvm/java-8-oracle/bin/java -Djavax.net.ssl.trustStore=/var/lib/bamboo/cacerts SSLPoke <mailserver.domain> 443
but i still get this error when the server should be sending mails:
The mail settings you entered were not valid. Error thrown was: javax.mail.MessagingException: Could not convert socket to TLS; 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
i've figured it out, there was a different certificate for the Port 25 then Port 443. So adding this to the truststore did the trick.
Additionally i needed an receiving connector (the server being exchange), because bamboo didn't seem to support ntlm auth.
Thanks for your feedback!
Some mail servers have their own specifications that may cause this configuration to be tricky.
If you want to double check your configuration prior to follow my suggestion, please make sure that Bamboo is using the exact same Java implementation and trust store. It might be the case that other Java implementation is being used therefore causing this issue.