An invalid certification path error 500 occurs when validating Web Requests in Automation

Summary

Automation action Send Web Request shows response code 500 and throws the error "Unable to find valid certification path to requested target" in Jira Service Management Cloud.

Diagnosis

The following error is thrown when we attempt to send a web request using Automation:

When the Automation Send Web Request action returns HTTP 500 with Unable to find valid certification path to requested target or the documented exception, identify the problem as certificate-chain validation on the target server.

Cause

The target server is not presenting the intermediate CA certificate during the SSL/TLS handshake, commonly because the intermediate certificate was not installed correctly.

Solution

If you own the target server, reinstall the intermediate certificate or confirm it is installed in the same place as the domain certificate. Otherwise, contact the Certification Authority. Do not use a TLS bypass or client-side workaround.