The advent of system-wide accessibility services on mainstream touch-based smartphones has been a major point of inclusion for blind and visually impaired people. Ever since, researchers aimed to improve the accessibility of specific tasks, such text-entry and gestural interaction. However, little work aimed to understand and improve the overall accessibility of these devices in real world settings. In this paper, we present an eight-week long study with five novice blind participants where we seek to understand major concerns, expectations, challenges, barriers, and experiences with smartphones. The study included pre-adoption and weekly interviews, weekly controlled task assessments, and in-the wild system-wide usage. Our results show that mastering these devices is an arduous and long task, confirming the users’ initial concerns. We report on accessibility barriers experienced throughout the study, which could not be encountered in task-based laboratory settings. Finally, we discuss how smartphones are being integrated in everyday activities and highlight the need for better adoption support tools.