You're able to create Playlists via Windows Media Player 10. Please refer to the below steps.

1. To create a playlist, connect COWON S9 to the PC and launch Windows Media Player 10.
2. Go to [Library] and click the right mouse button on a file.
Then choose [Add to - Additional Playlists]
3. Create new playlists and confirm it via [Add to]
4. Select the files and click the right mouse.
Then choose [Add to - the created playlist].
5. Go to [Sync - Set up Sync].
Check the playlists and click 'OK' button.
6. Save the selected playlists in the "playlist" folder in COWON S9.
7. Disconnect COWON S9 from the PC.
You can confirm it via [Playlist] folder.

Before you create playlists, please select MTP mode by changing USB connection.
[Settings] - [Systems] - [USB Mode]-[MSC or MTP]

While in "MTP" mode the player will only be able to transfer files through "Windows Media Player" or your online music store software. Drag and drop capabilities will be disabled. If you set the player to "MSC" mode, the player will show up as a removable drive, drag/drop capability will be enabled and recognition from the Jetshell program will be enabled.

Please note: To activate MTP/UMS settings for USB Connection you will need to turn restart the unit.