The radio isn't a PC so it's not going to read the files as a file manager would. It's just not that sophisticated. My guess is it takes the files and lists them together. I've never experimented to find out exactly what the sorting capabilities of the file system in the radio are, I just put an old 5th Gen iPod in there. The old 5th Gen iPod charges via pins 11 & 12 of the 30 pin connector, that's what the 2009 Navi has for charging so it works well.
I've still got my CF card in there with 1000 songs on it but it only reads 512. I spent the money on the CF card and don't have a camera so I just left it in there.
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