Hi Big Sponge,
I am sorry to tell that this issue is out of our support. It is actually supported by Sony. I would suggest you to contact Sony support. However, you can try the following basic steps, but if the issue still persists, I would request you to contact Sony for the support.
Here are the steps through which you can sync your music from media player to Player Playstation Portable:
1. Hook USB cable between the PSP and PC .
2. On the PSP under Settings, select USB connection .
3. Your Vista PC should recognize that the PSP is connected. The PSP should be displaying "USB Mode".
4. On the PC add music to the removable drive that represents your PSP memory stick. Put the music in the Music Folder.
You can also go through these steps:
> Step 1: Connect the portable music player to the computer through the USB port. MP3 players and other updated portable devices all have this capacity, which is intended for managing media files easily.
> Step 2: Open Windows Vista, and then click "Sync." If this is your initial try at using the device, your system may choose to sync files automatically or manually depending on the capacity of your music device.
> Step 3: Click the "Finish" button. On automatic mode, the entire library will be synced to your player's playlist instantly. In manual mode, however, after you hit the "Finish" button, you will still have to select the playlist you would like to sync with your portable music player.
> Step 4: Select files to sync. Even if your system chooses to operate in automatic sync mode, you can select the playlists that you would like to sync with your portable device. To do this, hit the arrow under the "Sync" button, click the device you are using and then hit "Set Up Sync."
> Step 5: Add your playlists. Click the "Available Playlist" button, select the playlists that you would like to include, and click "Add."
Hope this helps.
Thank you.