One important aspect of special education research that makes it complex is the variability of the disability categories being studied. This study used the context of Individualized Education Program (IEP)/transition planning and National Longitudinal Transition Study 2012 (NLTS 2012) student and parent survey items associated with this context to illustrate the challenges of grouping disability categories. We examined how disability groupings are treated similarly with respect to their transition planning experiences across different survey items. Findings illustrate that the 12 transition-related disability categories can be empirically formed into four clusters according to their IEP/transition planning meeting experiences. Results indicate that regardless of the scale used, these groupings are relatively consistent (e.g., autism, multiple disabilities, and orthopedic impairments were always together), but different from groupings based on theory or another set of items (e.g., self-determination). Implications for practice and future research are discussed.