NOTE: This tutorial is based on functionality in Windows Media Player 11 for the Microsoft Windows XP and Vista operating systems.  Windows Vista ships with WMP11 installed; Windows Media Player 11 must be manually installed in Windows XP. You can download it here free of charge if it's not already installed.  The tutorial below shows screenshots from Windows Vista, but is also applicable to Windows XP users.

Windows Media Player 11 (WMP11) allows you to transfer audio files to your Windows Mobile Pocket PC or Smartphone.  Although Windows Media Player is light years behind other jukebox software (most notably iTunes), it is one of the few tools you can use to manage the music on your Windows Mobile device. 

To begin, create a playlist in WMP11 on your PC.

 

Once you've constructed a playlist that includes the songs you'd like to transfer to your Windows Mobile handheld, make sure that your handheld is connected to your computer via ActiveSync (Windows XP) or Windows Mobile Device Center (Windows Vista) and select the "Sync" tab at the top of the WMP11 screen.

From the "Sync" screen, you can choose where on your Windows Mobile device you'd like the audio files stored.  In the example below, we chose to transfer the selected MP3 music files to our T-Mobile Wing's microSD flash memory card:

 

If you would prefer to copy music to your device's internal memory, use the Next Device feature (shown above) to change the destination to the internal memory.  We highly recommend that you invest in a flash memory card if you're planning to use your Pocket PC or Smartphone as a music player.  Check your device literature to see which format of memory card you can use.

Drag the playlist you wish to sync to the device to the Drag Items Here section of the right-hand column: 

 

Once you've selected the storage destination, and you've made sure that the music selections you've made will fit, click . 

The syncing process will begin:

 

Allow this process to complete.  Following the sync, an updated listing of the contents of the destination will be displayed: 

 

The transfer is now complete.  When you open the Windows Media Player Mobile on your Windows Mobile device, the transferred files will now show up as available audio tracks:

You can also move audio files to your Pocket PC, Pocket PC Phone or Smartphone manually with ActiveSync or Windows Mobile Device Center.