The release of Apple’s iPhone was one of the most intensively publicized product releases in the history of mobile devices. While the iPhone wowed users with its exciting design and features, it also angered many for not allowing installation of third party applications and for working exclusively with AT & T wireless services (in the US). Besides the US, iPhone was only sold only in a few other selected countries. Software attacks were developed to overcome both limitations. The development of those attacks and further evaluation revealed several vulnerabilities in iPhone security. In this paper, we examine some of the attacks developed for the iPhone as a way of investigating the iPhone’s security structure. We also analyze the security holes that have been discovered and make suggestions for improving iPhone security.