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No... actually RMM pretty relentlessly and undefeatably arranges the tracks alphabetically by title


This is because the order in which Windows gives you the files is fairly arbitrary, and is not necessarily related to the order in which they appear in the list.

Because most people do have them sorted alphabetically, and thus expect them to be imported alphabetically-sorted, and because of this arbitrary ordering in how Windows hands over the names, we simply opted to always sort them alphabetically.

That, and the fact that alphabetically-sorted is a spot on match for how I name my MP3 files, and how I want them sorted

What you can do is this:

In "My Music", click on Playlist / Rio DJ to bring up the wizard. Choose to create a new mix. On the "Select Tracks" page, choose "Select music where...". Then choose "Genre" and "Favorites", and click Next.

On the next page, choose "Random order". Then work through the other pages in the wizard. When you get to the "Use the mix" page, choose to create a playlist.

Then you can send this playlist to the player. To regenerate the list, just go to the Rio DJ again and select "Use an existing mix". It'll generate a new playlist with the same parameters.
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-- roger