Seems I can't be of much help I'm afraid. While I get the basic gist of what you're doing, Java isn't my cup of tea, shall we say.
Something that did occur to me: Have you tried running the server from a windows machine? Perhaps Wine is somehow "translating" one way or the other, and getting it wrong the first time.
When you compared packets in Wireshark, did you compare the first and second packet sent using the file selection dialog, or the difference(lack thereof) between textbox and dialog?
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