This study extensively evaluated the resistance to moisture damage and thermal cracking of hot-mix asphalt (HMA) mixtures with high recycled asphalt pavement (RAP) content (up to 50%) from field sections on provincial Highway 8 between Gimli and Hnausa in Manitoba, Canada. A comparison between the properties and performance of the field-produced and laboratory-produced mixtures was also conducted and was included in this study. HMA mixtures with 50% RAP resulted in acceptable resistance to moisture damage and thermal cracking. The use of multiple freeze–thaw cycles provided a better characterization of the mixtures' resistance to moisture damage. Acceptable correlations were observed between the estimated critical temperatures from the blending chart and the measured ones from the recovered asphalt binders. Overall, laboratory-produced mixtures could be used to evaluate the relative resistance of the field-produced mixtures to moisture damage and thermal cracking.