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The iPhone by Apple has taken the mobile world by storm since its original release in 2007. At that point in time, the only way to target the iPhone was by either writing a web application or jailbreaking the iPhone. Neither were very good options. Writing a web application for the iPhone is not difficult, but it doesn't take advantage of the native capabilities of the device. Jailbreaking an iPhone relies on the owner of the device to install a piece of software that sidesteps the iPhone's security schemes and official distribution mechanisms. There are several issues with jailbreaking:
Jailbreaking requires the iPhone's owner to perform the operation. Many iPhone users are not technically proficient enough to do this.
The legality of jailbreaking is unclear. It is not clear where jailbreaking falls within the Digital Millennium Copyright Act.
There are a series of unknowns with jailbreaking. How well can an iPhone that has been jailbreaked be upgraded to new versions of the iPhone OS? Will jailbreaking an iPhone open it up to security issues?