This paper investigates the influence of carbon filler type and 3D printing path strategy on the electrical conductivity and damage sensitivity of cement-based composites designed for structural health monitoring. The development of self-sensing, 3D-printed smart concretes is becoming increasingly important for monitoring the structural integrity of cementitious materials under dynamic loading conditions, such as earthquakes. These materials are particularly vulnerable to localized failures, often caused by inherent issues in the printing and curing processes. Such defects can compromise structural safety and limit service life, especially during critical events. To better understand these phenomena, the study evaluates the sensitivity of different samples to crack initiation and propagation, as a function of carbon filler type and printing path, offering insights into the effect of each material–process combination in enabling reliable damage detection for the creation of resilient, smart concrete structures. In particular two perpendicular orientations were considered for 3D printing, and their implications both in mechanical and electrical behavior. This analysis aims to evaluate the impact of the design of the manufacturing method for the printed structures and its varying effectiveness.