Background: Reconstruction of the orbital floor after maxillectomy can result in significant functional and aesthetic morbidity. Study Objective: To measure eyelid position, self-reported visual outcomes, and complications in patients undergoing concurrent maxillectomy and reconstruction with a patient-specific orbital reconstruction implant (PSORI). Design Type: Case series. Materials and Methods: Case series including 12 patients who received PSORI for orbital floor reconstruction after tumor extirpation. Primary outcomes gathered were diplopia, ectropion, and wound healing complications. Results: The majority of patients were men (75%) and the mean age was 53.3 years. Ten patients underwent free flap reconstruction with the majority receiving fibula free flaps (n = 6). Median follow-up was 415.5 days. Three patients (25%) experienced long-term complications, including diplopia (n = 1) and hardware extrusion (n = 3). Each of these occurred in the context of total maxillectomy and radiation. This prompted subsequent use of a modified implant design for the final six patients and the preferential use of a midface-degloving approach. These interventions eliminated extrusions in subsequent patients. Conclusion: PSORIs can be used for orbital floor reconstruction following maxillectomy in combination with free tissue transfer. Implant design is critical to reduce complications. The use of a midface degloving approach and a modified low-profile design was associated with a low rate of complications.