Students with extensive support needs often require intensive individualized instruction across domains. Research suggests that students with extensive support needs can achieve greater independence when evidence-based practices are used to teach independent transitioning skills. This study investigated the effects of video self-modeling (VSM) and the system of least prompts (SLP) on independent completion of transitional routines for a student with extensive support needs in inclusive school settings. Using VSM and SLP, the student learned to complete three transitional routines with greater independence. Generalization of independent transitioning skills to music class was also measured. Results showed a functional relation between the VSM/SLP intervention and independent completion of transitional routines. The findings of this study provide several implications for practice for using VSM and SLP as a combined intervention to increase independent transitioning skills for students who previously relied on adult assistance to make transitions along with general education peers.