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The Rio Carbon is completely incompatible with iTunes (which uses AAC format). It only accepts mp3, wma, and some WAV's. The Rio Carbon is still the best mp3 player I ever owned, but since Rio doesn't make them anymore, it will never be compatible with iTunes. You can use it with Rhapsody's Mp3 Only service, or any music service that gives you the files in mp3 format - but you can't sync the songs through the music service's "synchronize function" - you have to download the files to a location on your computer, and then use the Rio music Manager to transfer the songs to your device.
The Rio Carbon will not play songs from iTunes unless they are in mp3 format. If you cannot download the songs in this format then I would recommend a program such as mediacoder to convert the tracks. I don't know why iTunes was recommended for the Rio but I would just use drag and drop into the folder called Music on your Rio.
I have bad news - I was completely unsuccessful in dragging tracks from the rio to my computer. You can load songs, but you can't "unload" them with the Rio Carbon.
Just in case your computer has capabilities that mine does not, try this:
Double-click "My Computer" on your PC desktop
Double click the Rio Carbon icon
Double click the "Music" folder
Try dragging a single music file from the "Music" folder window to your PC desktop - it will either work, or it will say that it cannot copy the file to the specified location.
Go to this part of the Rio website, and get the Plays for sure firmware update - even if you don't transfer any WMA files, this will help you get around the Windows Media Player 11 compatibility issue: http://www.digitalnetworksna.com/support/rio/product.asp?prodID=234
(WARNING: make sure the player is fully charged before doing this, or your player will be permanently lost)
Windows only.... Please post if you are not using windows...
Open My Computer with your Rio plugged in. Right click on your Rio carbon and click on format. Leave the default values - if it asks you something then use your initiative. Then click on format. Then
when it has finished formatting go to your firmware (can be downloaded
http://www.digitalnetworksna.com/support/rio/product.asp?prodID=235). Follow the instructions and then it should load the firmware onto your player. When it has done then your player should (in theory!) work properly.
On a windows computer go into my computer and explore your rio carbon folder. In there there should be at least 2 folders - Music and recordings. go into the music folder and all of your files should be there. Delete them all and start putting files on again.
If there are no files showing in the Music folder then go back to my computer and right click on your player and click on format. Accept all of the default values and click format. You will then need to download the firmware for your Rio. This can be downloaded from: http://www.digitalnetworksna.com/support/rio/product.asp?prodID=234
Once you have downloaded it and your player has finished formatting then load the update by clicking on it and follow the instructions to install it. Once this is done then your player will be completely wiped and you can the start putting music back on it.