<p>Despite international calls for inclusion, there remain challenges in high school and university settings as to how effectively students with accessibility requirements and/or disability (ARD) are accommodated. Given the scarcity of literature investigating students’ experiences across these settings and students’ voices often unheard, this study sought to determine what students considered was the context which best catered to their needs, the beneficial characteristics of the support available, and what it was about each setting that underpinned this. These two settings have differing strengths and contextual constraints, including the level of responsibility placed on students to advocate for and seek support. Of the 62 university students with ARD, the number selecting high school, university, or neither context as best catering to them, were almost equal. Students’ decisions were predominantly driven by considerations of the culture, processes, and nature of seeking and receiving academic and wellbeing support in each setting. For almost a third of students, high school provided an environment which encouraged support seeking, facilitated the ease of the process via familiar and caring teachers, and was a place of guaranteed assistance. A similar portion found university accessibility and wellbeing staff provided them a feeling of care and being understood, that there were effective formal academic and wellbeing support, and this was provided in a way which bolstered their feelings of agency and control. These positive attributes were not experienced consistently by all. Implications, including of the strengths and constraints which may be inherent within high school and university structures, are discussed.</p>