Deformational head shapes are most often treated through repositioning therapy (RT) and/or cranial remolding orthotic (CRO) treatment. However, there is conflicting evidence about the effectiveness of each method, and treatment compliance is suspected to affect treatment effectiveness. This study examines participant adherence with these treatment methods and explores if cranial correction is related to compliance. This study also reviews effects of developmental milestones and explores other potential impacts on compliance. A total of 45 infants with cranial deformation were consented and those with congenital muscular torticollis (CMT) concurrently received physical therapy. Infants were followed from 2 to 12 months of age and initially assigned to RT. Caregivers continued RT until the head shape corrected, caregivers chose to switch to a CRO, or infants turned 12 months of age. All participants were scheduled for a final visit at 12 months of age. Throughout treatment, caregiver surveys were used to examine compliance and developmental milestones. Results show promise for future investigation into the relationship between treatment modalities and adherence with treatment for deformational head shapes. Our findings provide preliminary support that treatment adherence may be linked with treatment success and concurrent enrollment in physical therapy increases patient compliance.