Fitting pediatric patients with orthotic and prosthetic devices, while challenging, can be extremely rewarding and fulfilling. However, the process of fitting a child is truly different from fitting an adult in terms of understanding the child’s individual growth with respect to kinesthetic, cognitive, and emotional development. Monitoring these interrelated clinical and contextual values with the caregivers is crucial in developing a clinical plan, not only as it relates to the child’s mobility goals but also the child’s overall physical and cognitive development. Timelines of biomechanical and cognitive development serve as roadmaps to inform clinical decision-making, but detours are often necessary to adapt the original plan to meet the patient’s needs and shifting contextual values.