Today’s smartphone interactions are typically designed with one primary preset, accompanied by customization settings that can be manually adjusted. To promote the creation of contextually aware experiences, researchers have highlighted the factors that influence mobile device usage in the ability-based design framework. This paper expands upon existing frameworks and contributes to an empirical understanding of smartphone accessibility. Through a 10-day longitudinal diary study and video interview with 24 individuals who do and do not identify as having a disability, the research also illustrates the reactions of reattempt, adaptation, and avoidance, which were used in response to a lack of smartphone accessibility. Despite experiencing scenarios where accessibility settings could be leveraged, 20 out of 24 participants did not use accessibility settings on their smartphone. A total of 12 out of 24 participants tried accessibility settings on their smartphone, however identifying accessibility was not for them. This work highlights the need to shift current design practices to better serve the accessibility community.