Along with the decrease in sudden infant death syndrome due to the successful “Back to Sleep” Campaign, there was a reciprocal increase in cases of positional plagiocephaly (PP). The prevalence of PP significantly rose from approximately 5% to upward of 46% at age 7 months. Consequently, clinicians have seen a surge in the number of patients presenting with head shape abnormalities. Not only does this increase in patient volume pose a logistical problem to clinics, but it also poses a potential risk to patients with craniosynostosis, whose head shape anomalies are similar to a “needle in a haystack” of patients with more common PP. This review explores the causes, risk factors, and treatment options of PP and craniosynostosis, along with the differential of head shape anomalies based on phenotypic presentation. In doing so, we hope to provide pediatric care clinicians with the tools necessary to effectively evaluate and manage patients with head shape abnormalities. [ Pediatr Ann . 2023;52(1):e10–e17.]