Sync iPod with Windows Media Player 10
Cameron says, "Hello, My name is Cameron, I NEED HELP! I want to put music on my iPod from Windows Media Player 10, but it won't let me put music on it to sync!"
This is by design. Apple wants you to use their end-to-end experience of iPod-iTunes-iTunes Music Store. The easiest way to connect your music collection with your iPod is through iTunes. Windows Media Player does not natively support syncing with any of the iPod line of players and likely never will. There are a few third-party solutions designed to bypass iTunes as an interface for your iPod.
XPlay
At the moment, the best option for integrating iPod synchronization with Windows Media Player is XPlay. The software costs $29.95 and readily integrates iPod synchronization into the Windows shell. You can synchronize music files from the Sync tab in Windows Media Player 10 or drag-and-drop files to your iPod from Windows Explorer. The one trick to pay attention to in Windows Media Player is the appearance of two variations of your iPod. One version is listed with the name of your iPod and a drive letter like this: Your iPod (N:). A second variation only lists the name of your iPod. Be sure and use this second version or the tracks you sync won't show up in the iPod song database.
A second thing you need to set is in the properties for the iPod. On the Quality tab, Windows Media Player defaults to converting files for your device. Make sure this is unchecked or WMP will attempt to convert audio files to WMA format before transferring to your iPod. You also need to make sure the audio files you transfer are MP3 format files because iPods can't play WMA files and Windows Media Player will not convert to MP3 when transferring to a portable music player.
Media Monkey
The standard version of MediaMonkey is one way to sync files to an iPod without using iTunes. My personal experience is less than stellar with this option with an iPod mini manufactured in 2005, with frequent device errors. As an app for managing music, MediaMonkey is generally quite good, but my experience in combination with an iPod isn't so great. Your mileage may very. MediaMonkey standard is free, so taking it for a spin won't hurt your wallet.
Musicmatch
Beware the Musicmatch iPod support. At one time Musicmatch supported iPod synchronization via a plug-in. The app still mounts your iPod as a hard drive and transfers songs as if you could play them back, but the tracks are stored in hard drive space unrecognized by the iPod interface.
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