This chapter reconnects one of the authors with the mother of a young child, labeled on the autism spectrum, who has transitioned from an inclusive child care setting to a self-contained special education classroom. The conversation uncovers the complexities of understanding her child’s needs and advocating for an optimal educational environment and comprehensive supports. The meeting with this family takes place at a time when they are still coming to terms with their different understandings of their child’s diagnosis and their visions for his future.