I have to admit, that there is no really functioning GUI for the rioutils. Meaning that if I want to upload mp3 files to my Rio500 under Linux I have to use the command line (and even the command line seems to be somehow instable as the rpm was created a while ago and compiling fails under the recent Linux releases (Red Hat 8,9, Suse 8, 9). So I used first the Rioport AudioManager 3 under VMware. It is slow and the GUI is as bad as it gets (bloatware). A really cool replacement program for Windows is Riositude. It's much faster, easier to use and takes not even 200 KB disk space. It works great from VMware provided I start it up immediately after plugging in my Rio500. Otherwise the Linux takes over (I guess a usb kernel module is loaded automatically upon plugging in the Rio). The kernel module has to be removed manually by "sudo /sbin/rmmod rio500" to allow VMware to control the Rio. To check which kernel moduls are loaded, use "/sbin/lsmod". I should somehow get rid of this module if I want to stick to Riositude/VMware to operate my Rio. There are of course other programs for Windows, that can do a similar job, e.g. Rio FXP. Unfortunately this one didn't work for us under WindowsXP. A listing of Riosoftware can be found at rioworld.org.