Thanks for the feedback and test. I am able to re-produce this now. Not sure though, how our final test case should look like though.
A couple of questions though. AFAICT, the annotation metadata cache of Class only gets invalidated if one uses instrumentation (byte code modifications). Are you using that in your use case? You are also using Validtor#validateProperty in your test. Is this what you use in production as well? I am asking since switching to Validator#validate seems to make the test pass.

Last but not least, if I'd push a SNAPSHOT version to the Maven repository, would you be able to verify that it works in your scenario?