People who bought the original iPhone will remember perhaps the most annoying original feature: The long sync. That is, when you plugged the iPhone into iTunes it took forever for it to complete its syncing process. The main holdup was the backup process, that would take a ridiculous amount of time to complete, each time. Luckily, Apple fixed the issue with subsequent updates to the iPhone, and sped up the backing up process to mere seconds. But with iTunes 9, things are starting to look grim again. One main culprit is what should be a nice, new feature in iTunes 9 called "Automatically fill free space with songs." It does exactly what it says, finds songs to put on your iPhone to fill it up. This is great for people like me with too large of a music library to sync it all with the iPhone, and who don't really use playlists (the main way to sync music to the iPhone). Unfortunately, if you click this "Automatically fill free space" option, it seems that sometimes it wants to remove and replace much of the random music. If you have a 32 GB iPhone, that is going to take a while. TechCrunch50 Conference 2009 : September 14-15, 2009, San Francisco