My iTrip doesn't seem to be working.

Make sure your iPod has the latest firmware. Connect your iPod to iTunes, and highlight it when it appears as a "device" in the left column. Under the Summary tab, choose "Update" to update the firmware.

It's also a good idea to try a "soft reset". With the iTrip plugged into the iPod and the iPod turned on, hold down the Menu and Select buttons until an apple appears in the screen. Then you can let go and wait for the iPod to restart. After it restarts, try playing a song and see if the iTrip works.