The aim of this paper is to clarify some important aspects associated with the possibility to detect degraded compression and bolted joints in power transmission lines using a time-domain reflectometry (TDR)-based remote monitoring. The optimization of a TDR-based remote monitoring method is discussed, studying the effects of the source impedance, source-to-line connection, line characteristic impedance, and scope settings, providing useful guidelines for a future method and instrumentation refinement. The experimental results are presented consisting in the inclusion of lumped resistors of several values along a 130-kV power transmission line. The minimum detectable resistance is discussed based on the present available hardware. The TDR-based method is shown to be able to also identify the main features of the line layout such as phase transpositions and different heights of adjacent towers. This paper represents a preliminary base to keep developing the proposed method, with the aim to overcome the actual limitations (costs, reliability, etc.) in power line monitoring.