NullPointerExceptions aside there are 3 failing tests left. The problem with them is that currently we handle "unwrapping" not per constraint, but per property. This would need to change to make your use cases work. I guess we worked under the assumption that either all constraints apply to the wrapper or all to the wrapped value. I need to dig deeper into the code to see how we can support your use case. At first glance your tests looks reasonable.

On a tagent, I noticed that the results differ between validate and validateProperty. There must be another bug in the validateProperty code path.

Nice test case btw, I could just drop it into our code base. We will investigate the remaining failing tests asap.