This study used a mechanistic framework (i.e., surface free energy) to evaluate the moisture susceptibility of warm mix asphalt (WMA) with three different WMA additives, namely, Sasobit, Advera, and Evotherm. The surface free energy (SFE) components of modified PG64-22 asphalt binder with different percentages of WMA additives and selected aggregates were measured in the laboratory. The wettability, the work of adhesion, the work of debonding, and energy ratios were estimated in order to assess the moisture-induced damage potential of combinations of modified asphalt binders and different aggregates. The results indicate that Sasobit and Advera are able to reduce the moisture susceptibility potential of the mixes, but their use is not recommended with highly acidic aggregates such as granite. Evotherm resulted in the highest increases in wettability, total surface free energy, and increased work of adhesion and a reduction in the work of debonding, resulting in a better possible aggregate coating with asphalt binder and lower moisture susceptibility with all types of tested aggregates relative to those of other WMA additives. Furthermore, tensile strength ratio (TSR) tests were conducted on Advera and Evotherm-modified and neat (unmodified) asphalt mixes, and the results were compared with those from the SFE test. It was found that the SFE approach is a better indicator of moisture susceptibility than the traditional TSR test. The findings of the present study would help the highway engineers and agencies to better understand the moisture damage potential of flexible pavements constructed with WMA technologies.