Mobile technology is a new frontier for accessibility. Although mobile developers need solid guidelines to provide accessible experiences, there is a limited number of empirical research on mobile accessibility of different mobile platforms that work through various assistive technologies. In this context, more information is needed to understand both usage patterns and hardware/software platforms to guide decisions to meet the needs of people with disabilities who use mobile devices. This study, which is a pilot study of a long-term research, evaluates the accessibility of selected built-in and third party iOS applications in the iPhone and iPad through an extensive accessibility test with two blind users who are novice users of touchscreen mobile devices. This qualitative study is based on a multi-method approach, which consists of a background questionnaire, task observation, and a structured debriefing interview. The study also employs observation methods of data collection in order to gain better insight in mobile accessibility. The participants are demanded to execute three different tasks on each platform by using VoiceOver, which is the built-in screen reader in iOS. The participants are observed during the task executions and the “think aloud” procedure and video recording of the participants collected additional data. A short debriefing interview was also made to gain a detailed insight into the user experience. The findings reveal significant accessibility problems caused specifically by design of the graphical user interface features of the applications and limitations of the screen reader. Finally, as part of future research directions, preliminary guidelines are proposed to improve accessibility for iOS applications in both platforms.