This paper investigates the effect of water exposure on three different crack sealants commonly used in cold, moderate and hot climates. It is hypothesized that water penetrates into the interface between crack sealant and substrates causing progressive adhesion failure and that the rate of failure varies depending on the sealant's surface chemistry as relates to its interaction with water molecules in different environmental conditions. Accordingly, this paper measures the change in sealant's adhesion strength and surface energy before and after water conditioning. To study adhesion strength and its change due to water conditioning, three different types of sealant were tested using Direct Adhesion Tester (DAT). It was found that the adhesion strength of all three crack sealants reduces due to water exposure. In addition, to evaluate the surface properties and water phobicity of each sealant, the contact angle between a droplet of water and sealant surface was measured before and after conditioning at different temperature. The objective of the latter experiment was to determine whether sealants susceptibility to water would vary with pavement surface temperature. To do so, a sessile drop method utilizing FTA-1000 was used to determine the contact angle for each of the aforementioned water-sealant pairs at different temperatures. The results obtained were further used to calculate the work of adhesion at each scenario to be correlated to mechanical adhesion strength measured with DAT.