PSPWare Icon    Using automatic syncing
 

For the best experience, PSPWare is meant to be used with automatic syncing enabled. Using several automatic syncing options, you can have PSPWare automatically sync your selected music, photos and movies as soon as you connect your PSP to your computer. This means that, for example, you can make changes in iTunes and PSPWare will automatically apply these changes to your PSP without you having to change any settings within PSPWare.

You can change the automatic sync options in PSPWare's "Advanced" section. The best settings to start with are to have "Perform sync when a PSP is connected" and "Eject the PSP after syncing" checked.