mvn test -Dtest=SnakeCaseConverterTest
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Which version of swagger-core do you use?
Wouldn't hurt trying. I don't recall specifically if there were related bugs.
So there's probably a bug with regards to the Optional interpretation like you said, and you can still override it using the previously suggested way (I agree, it's ugly, but it would work).
There's definitely room to open an issue about it on swagger-core.