Could not install Gradle distribution from ‘https://services.gradle.org/distributions/gradle-6.5-all.zip’

Yes, I have full chains (root, intermediate, server) in both cases. The gradle.org certificate has a SAN of *.gradle.org, so it’s good for services.gradle.org as well.

Are you saying that you don’t see anything but a single self-signed certificate when accessing these domains through your proxy?