BigBoss, one of the native (jailbroken) iPhone application programmers, says that jailbreaking iPhones will live on long after firmware 2.0 is released.

He posted this over at Sleepers.net on 13 May 2008:

Q: Will I still need to jailbreak on 2.0?

A: Probably yes. Most apps that are cool today will not run on the SDK. This is because Apple has very stringent rules as to what an app is allowed to do and not do. Apps cannot operate on system files, cannot work outside of their own apps directory or outside of the users directory. This is great for things like games. But summerboard, customize, categories, bossprefs, all these sorts of apps are impossible. Also, apps cannot stay running when you press home with the SDK. That means apps like colloQ, Mobile Chat must disconnect when you press home. Think of how annoying that is! You think emulators will be cool? Well there will be no way to get the ROMs onto the device. In short, jailbreaking will be very much alive because the SDK is just not enough.

The part about apps not being able to run in the background when you press the home button is still true, even after yesterday's WWDC keynote by Steve Jobs. The apps cannot run in the background, but a service will be created by Apple that will run in the background and receive application updates over the network. This new service is designed to scale as more apps require it in the future. This would allow an instant messaging client to continue to receive updates even after the application has been exited (similar to the way that an SMS notification pops to the screen even when the SMS app is not running). But there will certainly be a few apps for which even this will not be ideal. And, there will be many apps that Apple simply will not allow on the AppStore because they hack the OS or do other sorts of things that Apple frowns upon.

So, I guess we'll all still be jailbreaking our iPhones. I'd certainly prefer to not need to do this in order to run many of the apps that I'm currently using, but if Apple isn't going to play the game that many developers and consumers want to play, we'll play it alone.