This study focuses on utilizing an energy harvesting system in which a dedicated Radio Frequency (RF) power source transmits RF power via rebar in a reinforced concrete column. The RF power is received and decoupled by a receiver, and is then rectified, boosted, and stored as electrical energy in a supercapacitor, later to be used to make measurements, process data, and communicate to the source via rebar. Two design attempts are presented in this study: (a) one uses single line conduction at 2.4 GHz for RF power transfer; (b) the other uses a more conventional two-line conduction at 8.0 kHz for RF power transfer. Both designs were unsuccessful: (a) the 2.4 GHz attempt demonstrated that no detectable RF power propagated through the concrete medium; (b) the 8.0 kHz attempt demonstrated that too much of the RF power was attenuated through the concrete medium for the energy harvesting circuitry work properly. A potential third design approach is posited in the conclusion of this study. In addition to investigating power transfer designs, a study on the energy harvesting circuitry was performed. A Two-Stage Dickson Multiplier was utilized in conjunction with a Texas Instruments BQ25504 Ultra-Low Power Energy Harvesting Circuit. For these two components to function best, it was shown that the BQ25504’s input filtering capacitor needed to be on the same order of magnitude as the charging capacitors of the Two-Stage Dickson Multiplier, otherwise, if the filtering capacitor was comparatively too large, it would short the output of the Two-Stage Dickson Multiplier. With that said, the lowest power input observed was at 7.83 dBm, but with lower input powers expected to be achievable. Nevertheless, since the second design attempt showed power losses were too significant, it was deemed that at present, unless the power transfer design were improved, then contemporary commercial off the shelf energy harvesting approaches are insufficient.