Still isn't working. I checked my Little Snitch configuration and made sure all iTunes connections were allowed. I disables Little Snitch anyway. Still didn't work. I restarted the computer after I disabled Little Snitch, and it still didn't work.
It can't be an issue with my router because I updated my dad's iPhone on a different computer in the house today.
I'm on iTunes 9.2 and I don't want to update to 9.2.1 because apparently it screws with the new jailbreak.