I'm guessing that the head unit must be using some information from the ID tag of the music file rather than sorting it based on the file name. To check this out, just write 2 tracks on the USB device. One with say file name A.mp3 and other with file name Z. mp3. Then manually edit the ID tag of the mp3 file so that all the tag details of file A read as "Z", and file Z read as "A". Artist, track name, date etc, everything. Plug it into the head unit and see what comes first.
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