Direct lightning strikes on overhead phase conductors result in high overvoltage stress on the medium voltage (MV) terminals of pole-mounted transformers, which may cause considerable damage. Therefore, introducing an efficient protection strategy would be a remedy for alleviating such undesirable damages. This paper investigates the optimized protection of MV transformers against direct lightning strikes on the phase conductors. To this end, first, the impacts of grounding densities (number of grounded intermediate poles between every two successive transformer poles) on the probability of overvoltage stress on transformer terminals are investigated. Then, the implications of guy wire, as a supporting device for ungrounded intermediate poles, on reducing the overvoltage stress on transformers, are studied. Finally, the role of a surge arrester in mitigating the overvoltage stress of non-surge-arrester-protected transformer poles is scrutinized. The investigations are conducted on a sample MV network with 82 wood poles comprising 17 pole-mounted transformers protected by spark gaps. To provide in-depth analysis, two different poles, namely creosote- and arsenic-impregnated poles, are considered under wet and dry weather conditions. A sensitivity analysis is performed on grounding distances and on a combination of guy wire and grounded intermediate poles while taking into account soil ionization. The results provide a clear picture for the system operator in deciding how many grounded intermediate poles might be required for a system to reach the desired probabilities of transformers experiencing overvoltage stress and how the surge arrester and guy wires contribute to mitigating undesirable overvoltage stress.