Jailbreaking your iPhone isn’t exactly a permanent thing. Every time that the boys and girls in Cupertino push out a new version of iOS and you choose to hit the upgrade button, your once jailbroken iPhone gets back behind its Apple-branded bars.
Sure, you can re-jailbreak your iPhone when the newest solution hits the net, but then you’re stuck having to manually re-apply all the purchases and downloads that you made through the jailbroken scene. The newest version of Cydia will help you, if only a little, in that regard.
No, it won’t automatically provide a new jailbreak solution the moment a new iOS is released, but it will be able to track your purchases and downloads made through the Cydia store. You just need to link up your account with either your Google or Facebook account.
Then, when you manage to re-jailbreak your iDevice, you can hop on over to Cydia and quickly re-apply the jailbroken goods you had once installed on a free device not long before. It’s not perfect, but that’s the price you pay for going against the big Apple.