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Make sure you have the correct version of Musicmatch and that you had installed the provided plugin for the PSS. I personally tried several hours of uninstalling and reinstalling everything until i get it to work.
Try "Pandora's Shoqbox" instead of musicmatch. If you don't like it or doesn't work you can also try Shoqbox buddy.
You have a file error: a system file may be missing or you have a format error on the SHOQBOX.
To fix this problem:
1. Connect the SHOQBOX to the computer using the supplied USB cable.
2. Plug your SHOQBOX into a wall outlet with the supplied AC adapter.
3. Launch the Device Manager at Start->Programs->Philips->Philips->PSS110 (or the model number of your SHOQBOX) on your PC.
* IMPORTANT: All music & content of your SHOQBOX will be erased once the factory setting is restored.
4. A dialogue box will pop up; click Restore and OK to confirm and start restoring the unit to its factory setting.
5. Follow the on-screen instructions to complete the restoration.
6. The Device Manager will close automatically once the success message is displayed.
7. Transfer a couple of songs into your SHOQBOX to confirm if the SHOQBOX has fully recovered all the files.
8. Close all opened applications and safely remove your SHOQBOX by clicking on the icon on your Windows task bar tray.
9. When prompted, ?The USB Mass Storage Device can now be safely removed from the system?, click OK and unplug your SHOQBOX.
10. Your player will display ?UPGRADING FIRMWARE?? once disconnected from the computer.
11. After firmware upgrade is complete, it will reset itself, showing the PHILIPS splash screen.
12. Press to switch on the player again.
Uninstall and reinstall the version fo the software directly from the Philips website: www.usasupport.philips.com
enter your model number
click on the version of your model number without the "B" at the end
Click on software & drivers
You will find clean, updated versions of the software there