There is something odd in the way the Java Stripe API wrapper configures SSL: When I use it in OpenLiberty (OL) container, it pick the configured SSL certificates store from the container, which is empty by default, and I start to see SSL errors like this one:

OpenLiberty/open-liberty#4377 (comment)

The issue was solved by adding either Stripe.Com or parent (DigiCert) certificates to the OL trust store configuration. However, this should be unnecessary, since Stripe API need only JDK's standard cacert , right?

I don't see the same issue with Auth0.Com or Amazon AWS JAVA SDK 2.0 java libs, all bypassing the container SSL configuration and working flawlessly (I presume with the default JDK SSL context and cacert files).

You can examine the 2 Java libs I mentioned - they are both on github - and see what you are doing differently.