Incoming mail has authentication problems after migration to cloud

[Michael Rudorfer]

I followed Atlassian's recommendation and migrated from my on-premise Jira to the Cloud version.

Migration worked quite well, only my incoming mail handlers are not working.

I configured the mail handler, just as on the old Jira, but when I click on Test, I keep getting this error message:

javax.mail.MessagingException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target while connecting to host 'MYDOMAIN.de' as user 'MY.USER' via protocol 'imaps, caused by: javax.net.ssl.SSLHandshakeException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target

MY.USER and MYDOMAIN are my user name and domain in the real error message.

Looks like some certificates are not in place or are not accepted.

Our certificates are from https://letsencrypt.org/

Any idea how to fix this?

[Daniel Ebers · Accepted solution]

Hi Michael,

this generic error message suggests there is a problem with the connection, more specifically it is about the SSL certificate as you already suspected.

There is a knowledge base article that some special certs are troubling but I could not find anything about Lets encrypt certificates:
https://confluence.atlassian.com/cloudkb/getting-certificate-error-when-connecting-atlassian-cloud-with-external-applications-using-godaddy-cert-815239674.html

I assume the mail server is under your control or at least controlled by your IT Team?

Cheers,
Daniel

[Michael Rudorfer]

Hi Daniel,

Thank you for your quick answer.

This was the missing hint. My friend ("the IT department") had a closer look to the certificate chains and due to misconfiguration on our mailserver the certificate was not deployed properly. He was now able to fix it.

Mail handler now working fine :)

Cheers,

Michael