Cranial remolding orthoses are an effective treatment of deformational plagiocephaly. Typical treatment durations are well documented. However, treatment duration can be affected by multiple factors and may not be a true representation of the time necessary to achieve a successful clinical outcome. This study compared the time to achieve a successful clinical outcome against the total treatment duration for cranial remolding orthosis therapy in infants with deformational plagiocephaly. This is a retrospective study of infants treated for deformational plagiocephaly with a cranial remolding orthosis. A total of 300 infants with deformational plagiocephaly who were treated with a cranial remolding orthosis were grouped by corrected age at initiation of treatment and by severity of deformity. A successful outcome was defined as achieving a final cranial vault asymmetry of 5 mm or less. For the 226 infants who achieved a successful outcome, time to successful outcome and treatment duration were compared between the groups. The time to successful outcome depended on severity but not on age at initiation. The median time to successful outcome ranged from 6 weeks to 17.5 weeks, depending on the severity of the deformity. Time to successful outcome was significantly shorter than treatment duration for infants with an initial cranial vault asymmetry of less than 17 mm. Current treatment durations for infants with moderate plagiocephaly may be longer than necessary. Estimated treatment time lines should be based on the initial severity of the infant's deformity.