Q: I have downloaded roughly 2000 songs, but I have yet to see any album artwork in either iTunes or on my iPod. How do I get these to display on the iPod?
A: Album artwork importing is unfortunately not yet automatic within iTunes, except for those songs purchased from the iTunes Music Store. For more information on how to get Album Art into your iTunes Music library, see our iPod 101 tutorial on the subject here.
Once the album art has been added to your iTunes library, it will synchronize to your fifth-generation iPod, iPod photo, or iPod nano, provided that the “Display album artwork on your iPod” preference is set in iTunes.