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Accommodations can provide essential supports for PSE students with disabilities, but not all students access the accommodations they need for a variety of reasons. The current study is focused on the experiences of post-secondary education (PSE) students with disabilities and exploring how they develop a sense of well-being as they navigate their schooling and access accommodations. We interviewed 27 post-secondary students (average duration, 34 minutes) about their conceptions of well-being and their experiences accessing accommodations. Findings suggest that the decision to disclose their disability and seek accommodations in PSE is informed by the emotional calculus of risk and reward. Despite the rewards, disclosure was a risk that many students were unwilling to take. Implications for practice are discussed.