In this brief, the perspectives of special education administrators from Massachusetts and Indiana, who have been engaged in college-based transition services (CBTS), are shared. It summarizes the conversations they had during a fall 2019 Think College webinar and a follow-up discussion in summer 2020. Each administrator has had extensive experience overseeing CBTS in collaboration with their college partners. It is our hope their insights will inspire more special education administrators to support the students they serve with access to transition services in college-based settings.