Q: I’m unable to sync music to my iPod Classic using Windows Media Player. What am I doing wrong?
A: As you have discovered, the iPod isn’t compatible with Windows Media Player, as is. This has something to do with competition between Apple and Microsoft and their methods for protecting digital content.
There is an option that I haven’t tested, so I can’t make any promises about it. See this Web address http://www.mgtek.com/dopisp/ for information on a plug-in that claims to add the features you want to Windows Media Player. The plug-in costs $19.95, although you can install it and try it for free for 30-days.
An alternative is to use a different program than Windows Media Player. There is Apple’s own iTunes (http://www.apple.com/itunes/), as well as, MediaMonkey (http://www.mediamonkey.com/), and SharePod (http://www.getsharepod.com/).