Tony,
I've done it a few more times now, and it doesn't seem to matter which file. They're all .mp3's.
The software auto updated on install. I did it manually as well, no change.

To any one who might be reading this post as negative, and focusing on the bug:

The player effing rocks. Just fricking rocks. Using it feels as cool as my using empeg did when I got it the first day. 1/4 the size, same capacity as my first empeg and 1/3 the price, runs for 10 hours and has first class fit and finish. Absolutely spectacular.

KungFuCow: Just access via tags, like emplode. I haven't played with the synch function yet, this might do what you want. EDIT: There's also a file level interface (My Computer) I just hadn't noticed it.

-Zeke