Ive seen multiple threads since the release of iOS 5 about wireless syncing not working so I'm hopefully going to help everyone out with this one thread... - Wirelss syncing must be enabled on the summary page for your iOS device in iTunes. It's the second check box under the Restore and a update buttons. - The checkbox to open iTunes when the device is connected MUST be checked on the summary page as well. It's the first check box under the Restore and Update buttons. - Your iOS device MUST be connected to a power source to AUTOMATICALLY sync when your on your home network. Yes, you can start a wireless sync manually without being plugged into power by going to Settings > General > iTunes Wifi Sync and tap the Sync Now button. - You MUST have iTunes 10.5 installed and open for all of this to happen. - You MUST be on your home network. You can not wirelessly sync to your home library from work. If you've done everything above then it should start syncing within seconds of plugging in your device. You should see the spinning arrows in the top left corner. If it still does not work, restart your comp and iDevice. If it still doesn't work, then you have other problems. Hopefully this helps most people. These seem to be the outcome of most of the "my iDevice doesn't wirelessly sync" threads that keep popping up.