How medical students, their teachers, and school administrators understand disability appears connected to ongoing, unequal access to medical education for disabled people. The stigmatization of disability within medical education affects students' disability disclosures, yet few studies have explored how understandings of disability influence inclusion practices beyond individual student actions. This paper develops the concept of legibility, derived from a constructivist grounded theory study that examined disability inclusion at four U.S. medical schools through interviews with 19 disabled students and 27 school officials (faculty and administrators). With two dimensions (recognition and assessment of possibility), legibility demonstrates that knowing disability is relational, contextual, and equivocal. Drawing from the field of disability studies, the paper argues that the current paradigm of disability inclusion demands that students' disability experiences be highly legible to themselves and others, yet increased legibility comes with potential risk due to prevalent ableism. While individual interactions can shift understandings of disability towards greater inclusivity, systemic action that embeds liberating discourses of disability into medical education is needed.