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Background/Objectives: Virtual surgical planning (VSP) and CAD/CAM technologies have revolutionized complex maxillofacial reconstruction. While high-resolution imaging is critical for these workflows, the specific clinical impact of photon-counting computed tomography (PCCT) remains to be fully established. This prospective pilot study evaluates the feasibility and clinical utility of integrating PCCT into the preoperative planning and surgical workflow of complex maxillofacial reconstructive cases. Methods: This feasibility study included ten patients requiring complex maxillofacial reconstruction with microvascular free flaps. All underwent preoperative imaging with photon-counting CT. Primary endpoints included clinical assessment of osseous invasion, reliability of donor-site vascular mapping from a single acquisition, and compatibility of PCCT datasets with VSP/CAD-CAM platforms. Secondary endpoints included resection margin status, flap survival, and short-term oncologic outcomes. Results: PCCT provided high-resolution visualization of cortical and medullary bone, enabling detailed assessment of tumor-related osseous involvement. In selected cases, findings supported refinement of resection planning when prior imaging had been inconclusive. Spectral reconstructions reduced metal artifacts and facilitated precise segmentation for multi-segment osteotomies. Donor-site vascular anatomy was successfully evaluated within the same scan, supporting operative planning without additional imaging. PCCT datasets were fully compatible with the virtual surgical planning (VSP) software used in this study (CMX Portal, version 2.6.1158, Medartis AG, Basel, Switzerland; or ProPlan CMF, version 5.7.8.025, Materialise NV, Leuven, Belgium) in all cases (100%). Reconstruction was completed successfully in all patients, with 100% flap survival and R0 margins in all malignant cases. No technical failures occurred during imaging transfer or CAD/CAM fabrication. Conclusions: The integration of PCCT into the surgical workflow proved technically feasible and clinically impactful. This pilot data supports its potential to enhance surgical precision and preoperative planning in complex jaw reconstruction.