In this Voices: Reflective Accounts of Education essay, Carrie C. Snow reflects on her experiences as both a recipient of pull-out services as a young child and as a special educator. She highlights the complex nature of special education services and how their provision is rife with gray areas. Negotiating various tensions in decision-making around whether to provide push-in or pull-out services to students with special educational needs, special educators can embrace this sense of gray to create and sustain flexible practices that forefront quality learning for their students. She discusses ways that pull-out services for students with distinct needs can work to support their learning, as well as ways they do not. For students to cultivate a trust for schooling, feel an interconnectedness, and experience joy in learning, teachers' decisions around special education service delivery can never be cut and dried.