Things You'll Need
Instructions
Sync iTunes to PSP with doubleTwist
Download and install doubleTwist.
Connect the PSP to your computer using a USB cable.
Launch doubleTwist.
Select "Sony PSP" from the "Devices" section in the left-hand sidebar.
Check "Sync music with this device" and specify if you would like to sync your entire iTunes library or just select playlists.
Click "Sync" to sync your music.
Sync iTunes to PSP with iTunes Agent
Connect the PSP to your computer using a USB cable.
Download and install iTunes Agent.
Launch iTunes Agent. This will load iTunes Agent into the system tray notification area.
Right-click on the iTunes Agent icon in the notification area and select "Preferences," "New." You will be able to configure the device information for your PSP in the dialog box that loads.
Specify a "Synchronization Pattern" from the drop-down menu to set the folder structure used when syncing music to your PSP. There are three options:
Select the folder you wish to save synced music to on your PSP. This is where the music files will be transferred to on your PSP.
Click "Create" to generate a unique "Recognize by folder/file" string. The string will be long, and seemingly random, but it is necessary so that iTunes can recognize the device.
Select any iTunes playlists you would like to use in selectively syncing your PSP in the "Associate with Playlist" drop-down menu. Alternatively, you can leave this field unspecified if you intend to manually sync music to your PSP in iTunes.
Click "Save" once device settings are configured.
Launch iTunes. Your PSP device should appear under the "Device" section in the left-hand sidebar. You can configure the device to sync with your iTunes library as if the PSP were an iPod.
Sync iTunes to PSP with PSPWare
Download and install PSPWare.
Launch PSPWare.
Select the "Music" tab.
Select the playlists you wish to sync to your PSP or select the entire library.
Click "Sync Now" to sync your iTunes music to your PSP.
iTunes - Artist/Album/Track.mp3
Artist - Artist - Album/Track.mp3
Flat - Artist - Track.mp3