So, you have firmware 1.1.3 and just spent the $20 on a set of shiny new Applications, and now you have some basic questions. Well, here are some basic answers to the most asked questions. What happens when I Update my iPod to a newer firmware version, do I get to keep my Applications, or do I have to pay again? Due to the magic of digital rights management, or DRM, iTunes is smart enough to know that you have already purchased the Applications and won't make you pay again. Well, what if I have to restore my iPod and completely start form scratch? Again, we can thank our friend DRM for telling iTunes that you already purchased the Applications, and that it should go ahead and install them upon restore. Luckily, DRM keeps all of its information stored on your computer, as well as your iPod. Thanks, DRM Can I sync my friend/brother/azalea's iPod up to my computer and sync the Applications to their iPod? Unfortunately, no. The DRM is also smart enough to know that unauthorized devices should not be messing with your stuff and will not allow the applications to be installed on anybody else's iPod but yours. Why should those freeloaders profit off of your $20.00? What if I authorize their iPod to use/play/watch things purchased with my account? Sorry, your friend is out of luck. DRM knows which iPod is yours because it ties its information to your iPod's serial number. Only the iPod you purchased the Applications for can use them. -- It appears that I was given misinformation from the Apple support person. And it looks like it the Applications are synced by account and not serial number. Wait, wait, wait, wait, wait! Does this mean that I have to buy these applications once for every iPod that I own!? Unfortunately, yes. Yes it does. Is there any way around this? Why yes, yes there is. You will need to downgrade to an earlier firmware version, 1.1.2 or earlier, and wait for the Dev Team to release the ported 1.1.3 applications. Hope this helped, and as always, enjoy! Source: Apple.