Intramedullary fixation of proximal tibia fractures remains a challenging surgical technique, with malalignment reported as high as 84%. The pull from the extensor mechanism, the hamstring and iliotibial band, in addition to the lack of endosteal fit from the nail, has made surgical fixation of these fractures difficult. Commonly held principles to reduce angular deformity include ensuring adequate imaging, obtaining an optimal start and trajectory for the implant, and obtaining and maintaining a reduction throughout the duration of the procedure. Some adjunctive techniques to assist in the application of these principles include use of a semiextended technique, clamping, blocking screws/wires, and unicortical plates. Understanding the challenges involved in intramedullary nailing of proximal tibia fractures and considering a wide array of techniques in the orthopaedic surgeon's armamentarium to combat these challenges is important.