The purpose of this study was to examine how secondary students with severe disabilities (i.e., severe intellectual disability or autism, multiple disabilities) participate in extracurricular school clubs. Using a qualitative multiple case design, the experiences of three high school students were examined. Data were collected through interviews, observations, and document reviews. A single-case inductive open-coding strategy was utilized across all data sources in which codes and categories emerged, and a final cross-case thematic evaluation was conducted. The cross-case thematic analysis resulted in the following four overarching themes: (a) going with the flow; (b) social obstacles: on the outside looking in; (c) supports provided: too much, too little, just right; and (d) safety in numbers.