Well, really I should say they are related, not necessary the same problem. They both involve the same code. I'll leave them as separate issues though since they do deal with different logic branches.

I think I know what goes wrong with Date/Times (HHH-8807) so I'll try to reproduce that here.

Now that you mention that your case here does not use @Enumerated though I would actually expect this to work. Therefore I am uncertain how to go about testing it. Would be great to get your enum and entity that uses it as a base. Also, some more info in terms of how you think the converter is applied. Explicit @Convert? Auto apply? etc...