The focus of this research is on thermal contact resistance between a mold and its insert, specifically inserts made by additive manufacturing (AM). Using a thermal steady-state system and varying contact pressures (0, 50, 75, and 100 bars), we present experimental results of the thermal contact resistance at the contact interface between steel A (1.2344), obtained from an extruded rod, and steel B (1.2709), produced by laser powder bed fusion. Thermal tests were performed for unbonded and bonded configurations. Results showed that increasing the contact pressure allows the system equilibrium to be reached at lower temperatures. Furthermore, thermal tests showed that in the transition zone of the bonded configuration, a well-defined resistance is not formed between the two steel samples as it occurs in the unbonded configuration. For the unbonded configuration, the thermal contact resistance values decrease with increasing applied contact pressure, improving the system’s heat transfer.