The objectives of this study are to experimentally investigate the effects of the dielectric material and the package stiffness on the durability and the efficiency of a previously developed triboelectric-based instrumented knee implant prototype. The proposed smart knee implant may provide useful information about prosthesis health and its functionality after a total knee replacement (TKR) by routine monitoring of tibiofemoral load transfer without the need for any external power source. The triboelectric powered load sensing by the proposed TKR system needs to be functional throughout the entire life of a knee replacement. The power output of the triboelectric system depends on the surface charge generations and accumulations on its dielectric material, and the force that transmits through its housing into the tribo-materials. The properties of the dielectric material and the package stiffness can significantly influence the reliability of the proposed device. For such a TKR system, a compliant mechanism with the ideal material selection can improve its state of the art. We investigated the performance of three vertical contact mode triboelectric generators made with three different dielectric materials: polydimethylsiloxane (PDMS), fluorinated ethylene propylene (FEP), and polytetrafluoroethylene (PTFE). To investigate the effect of package stiffness, we tested two Ti–PDMS–Ti harvesters inside a polyethylene and a Ti6Al4V package. At 1500 N of sinusoidal loads, the harvesters could generate and of mean apparent power in parallel and single connections in the polyethylene package, which was 32 and 17 times greater than the power recorded in the Ti assembly, respectively.