I dont know if this will work for you guys but i had the same problem but when i download a new app the problem goes away. It works for me whenever this happens and hopefully it will work for you too, so just get some crappy free app then delete it later.
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Not always automatic. You do need to go into the apps tab while in iTunes (looking at the highlighted iPod) and select the apps to sync. As long as the box is checked next to it and you legitimately own the app and it is iPod Touch compatible, it should work without a hitch.
I think it is that you might have to restore your ipod to its original firmware and reinstall the apps. If this doesn't help, call apple and let them fix your itouch. Also these days, anyone that jailbreaks their itouch gets their itouch screwed because apple does not allow jailbreaking.
Try removing that app from your iPod, then download it again from the App Store (free re-downloads) or if it is on your computer, simply connect your iPod and upload it back onto your iPod. That always works for me.
I'm pretty sure it was asking for your iTunes password. Have you created an iTunes account yet? You need that account to download pretty much everything from the iTunes store, including free apps like AIM. Signing up for the account is pretty easy. Follow this link:
The easiest way to download to your iTouch is directly to your iTouch via the Apple Store. The Apple Store icon is already on your iTouch. Just make sure you are near an internet connection via Airport or Wi Fi. Click on "Download" on the selected app, and then wait a couple of seconds. Your iTouch will indicate when the download is done and the app is installed. You will see the new icon on your your screen page.
If you install from your computer, you will have to plug your iTouch into the computer and use the iTunes app to control what you download.
I hope that helps.
i dont think i can help you fix this but if you jailbreak your ipod, they make an app which helps you compensate for the broken home button. i stumbled across it the other day while surfin through apps in installer. look up "ziphone" in google and procede from there to find the app which fixes your problem! give me good rating if this helps