Students with extensive support needs (ESN) often require repeated individualized instruction across a range of instructional domains. Research suggests that students with ESN can learn greater independent skills when evidence-based practices (EBPs)m are used to teach independent transitioning skills. This study investigated the effects of a paraprofessional-implemented video self-modeling (VSM) and system of least prompts (SLP) intervention on independent completion of transitional routines for a student with ESN in inclusive settings. Results showed a functional relation between the VSM + SLP intervention and independent completion of transitional routines. Additionally, the paraprofessional received Behavioral Skills Training (BST) and implemented the VSM + SLP intervention with high fidelity. Moderate levels of generalization of independent transitioning skills for transitional routines were observed. The findings of this study provide several implications for practice for using VSM + SLP as a combined intervention to increase independent transitioning skills for students who previously relied on adult assistance to make transitions alongside general education peers.