I think you need to clarify a few things. ioFTPD doesn't use winsslwrap. The bundled 3rd-party ioGUI utility I believe does. I've never needed to use that feature since I only run ioGUI from the same machine the server is running on, but I believe winsslwrap (is that still supported?) is what needs to be configured correctly so look at it's configuration file...
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