Purpose: To present our approach to zygomatic osteotomy and repositioning using technological aids: virtual surgical planning, custom guides, and implants. Background: The zygomatic complex is highly 3-dimensional, establishing cheek prominence, facial width, and orbital morphology. Functionally, the zygoma supports soft tissues and is vital to mastication. The zygoma may require reconstruction after a variety of congenital or acquired conditions; however, Zygomatic Osteotomy and Repositioning (ZyOaR) is a complex operation with many technical considerations. The advent of virtual surgical planning (VSP) has enhanced efficiency, accuracy, and reproducibility, while permitting utilization of custom-designed guides and implants. There remains a paucity of literature on ZyOaR and its unique challenges. Methods: This case series includes all patients older than 18 years old undergoing ZyOaR with VSP between 2010 and 2024. Demographics and clinical etiology were noted. Outcomes included fidelity to preoperative plan, facial symmetry, mastication defects, and globe malposition. Results: Eight patients age 18 to 60 years old (mean = 38) met inclusion criteria. Three patients had congenital deformities, and 5 were post-traumatic. Follow-up time ranged from 1 to 50 months (mean = 17 months). There were no intraoperative or postoperative complications. No patient had visual changes at latest follow-up. Preoperative VSP plans were compared to postoperative CT scans, showing a high degree of fidelity. All patients underwent secondary reconstructive and/or soft tissue procedures to achieve final results. Conclusions: Zygomatic Osteotomy and Repositioning (ZyOaR) is inherently difficult, and there is a current gap in the literature on its unique technical challenges. We present 8 cases of ZyOaR using VSP for patients with a range of disease etiologies. The procedures were well tolerated and maintained high surgical fidelity. In our experience, keys to optimize ZyOaR include comprehensive analysis of regional bony and soft tissue anatomy, virtual planning with production and use of surgical transfer guides, and custom 3D printed patient-specific implants.