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Being an Apple product, the only way to upload music onto your ipod is exclusively through Apple's software: iTunes. Go to www.apple.com, and download and install iTunes. After this, upload your music into the iTunes library. Then, click and drag the songs you want onto your ipod in the right hand side of itunes.
The ITunes filters all music so it goes only (like WM and RP does) into their compatible, licensing paying devices. Just save the songs (MP3 or Wav) outside the ITunes folder and upload it directly into the 9008 or any other MP3 compatible.
So you are trying to upload songs onto the internet? Well, first of all, you are going to need a place to upload them to, then you would probably want to use windows to upload them, unless of course you have a better program. But before any of that happens, why are you trying to upload them, where are you trying to upload them to, what do you not understand that you want me to explain, and are you sure what you are doing is legal?
My suggestion is switching the file transfer protocol from MTP to MSC by accessing it under the Menu.
Once you do this, when the Lyra is plugged into the computer, it will appear as an external hard drive.
Format the hard drive and then drag and drop your songs and/or directories of songs onto the Lyra.
This is what I do, as I never use Rhapsody, URGE, or even Windows Media Player or MusicMatch to upload songs onto my RD2763.
Hope this helps!
I think that the problem is with the songs file formats.
Try checking that they are all mp3. if they aren't then you have to convert them using an "MP3 Converter" software. there all plenty on the web.
Goodluck
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