In this work preliminary yet comprehensive considerations are reported on the possibility for remote monitoring of degraded compression and bolted joints on high voltage overhead power lines. Measurements are performed on new, naturally aged, and artificially degraded joints to quantify the impedance discontinuity introduced along typical HV overhead lines. Numerical simulations, a preliminary time domain reflectometry (TDR) measurement campaign, and circuit simulations are performed on a real power line to study the TDR-based capabilities for the identification of the investigated joint impedances. This study sets the basic concepts to the development of a remote monitoring system for quantifying and locating degraded joints.