Syncing Windows Media Player files with iTunes, and thus your iPhone, is not difficult. The key is to use media folders shared by both WMP and iTunes and to limit WMP's automatic file detection features so you control the process. After iTunes has your WMP files in its sights, they are synchronized through your regular iTunes connection.
Syncing WMP Folders to iPhone
One of WMP's more powerful features is the way it hunts down and incorporates media files into its own library database. Upon the first activation of WMP, it searches default folders for files it can play. As you rip CDs or play files from other locations, WMP adds these as well.
The files remain in the original folders, so consolidating these for your iPhone requires manual transfer into iTunes. This can be done using one of two different methods. When your WMP files are transferred into iTunes, they will be uploaded to your iPhone during a regular sync with iTunes.
Automatically Add to iTunes Folder Method
Open WMP and locate a song or songs for transfer. Right-click on a song title and select Open File Location. Windows Explorer opens with the folder containing the song.
Expand the Music folder on the left side of the window to reach the Automatically Add to iTunes folder. Click and drag the song file to this folder.
iTunes Add Files and Add Folders
Open iTunes and click File. Choose Add File to Library to add a single song and Add Folder to Library to add a folder containing multiple song files.
Choose the file or folder to add to iTunes. Using a folder as an example, click the folder in the Explorer window and then click Select Folder. The chosen songs are added to iTunes.
Advanced Integration of WMP and iTunes
While you can move files manually between WMP and iTunes to sync with your iPhone, there are changes to both applications that will improve the way they work together. Changing these settings keeps song files synchronized between WMP, iTunes and your iPhone.
Open iTunes and click Edit, then Preferences and select the Advanced tab. Take note of your iTunes media folder location for use with WMP and then check the boxes for both Keep iTunes Media folder organized and Copy files to iTunes Media folder when adding to the library. Selecting these boxes gives iTunes control over where media files are stored.
Choosing to copy files to your iTunes media folder may create duplicate files on your computer. You can disable this option if you're comfortable managing your own media folders.
Click Edit, then Preferences and select the General tab. Click Import Settings and choose MP3 Encoder from the Import Using drop-down box. This directs iTunes to use the MP3 format when ripping audio from CDs, maintaining compatibility with WMP. Select quality settings to match your personal taste and file-storage capabilities. Higher quality creates larger files.
Windows Media Player Settings
Open WMP and click Organize, then Options and select the Rip Music tab. In the Rip Music to This Location section, change the folder to match the iTunes media folder location identified earlier. Change the Rip Settings format to MP3 for compatibility with iTunes. Uncheck the Rip CD Automatically box if you prefer to select file format at the time of ripping.
Click Organize, then Options and select the Library tab. Uncheck Retrieve additional information from the Internet, Rename music files using rip music settings and Rearrange music in rip music folder, using rip music settings. Disabling these settings prevents WMP from moving media files around in such a way that iTunes can't follow.
Third-party programs such as MediaMonkey, MusicBee and WinAmp can also bridge gaps between WMP and iTunes, but with WinAmp no longer in development and the M4A format supported in WMP version 12, these programs add steps to the iPhone sync process. These applications are at their best providing advanced audio features and alternatives to WMP and iTunes players.