Sync iPod with Windows Media Player

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, but if you use the link to NewEgg here, the price is $24.95. Xplay 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. The software is hands down the best music file manager for Windows. With recent improvements, it's also one of the best ways to sync your iPod without using iTunes. I highly recommend MediaMonkey.

UPDATE: I've removed MusicMatch from this list as of February 2009 because Yahoo no longer supports MusicMatch and redirects it to Yahoo! Music.

More Great iPod Tips

How to Copy Songs from your iPod to Windows

Improve iPod battery life

Using your iPod as a portable hard drive