Teachers of high school students with severe disabilities are charged with making decisions about educational programming that prepares students for life post-school. This includes decisions about using community-based instruction (CBI) to teach skills that students will need to participate in the community. This qualitative study investigated the factors 13 high school special education teachers considered when making decisions about whether to use CBI with 26 students with severe disabilities and the factors they considered when selecting skills to teach these students during CBI. Data were collected using in-depth interviews and analyzed using a constant comparative method. Findings indicate that program organization and individual student needs influenced teachers' decisions to use CBI. When selecting skills to teach during CBI, teachers considered the student's current and future needs, the classroom curriculum, skills needed in the community, and the student's ability to learn.