This study estimated highway pavement and bridge damage costs, and analyzed the adequacy of permit revenues to cover these costs. The study began with an extensive review of the literature on the subject, thus facilitating identification of the gaps in the existing practice and research. The developed framework includes the establishment of asset families, realistic types and timings of reconstruction, rehabilitation, and maintenance, traffic volumes and growth projections. The cost of damage was estimated for each asset family and age group, and the sensitivity of asset damage cost with respect to key policy and analysis variables was explored. Finally, the study examined cost and operational issues associated with the enforcement of overweight truck policies. In addressing the gaps in existing research, this study showed that the damage cost of highway assets due to overweight trucks is influenced significantly by the asset type and age. For pavement assets, the pavement damage cost estimates were found to range from $0.006 per Equivalent Single Axle Load (ESAL)‐mile on Interstates to $0.218 per ESAL‐mile on non‐national highways. The study also showed that non‐consideration of reconstruction or maintenance cost can result in underestimation of the actual pavement damage cost by 79% and 83%, respectively. The analysis also showed that the unrealistic approach of considering only rehabilitation treatments applied at fixed intervals can lead to as much as 86% underestimation of the actual pavement damage cost. The results also suggest that pavement damage cost is highly sensitive to the pavement life‐cycle length, interest rate, rest period, and the costs and service lives of rehabilitation treatments. For the bridge assets (classified on the basis of their superstructure material type), the incremental methodology was found to be suitable to estimate the cost of bridge damage due to overweight vehicles. This methodology determines and assigns bridge damage cost to all vehicle classes on the basis of vehicle axle configurations and usage frequency (vehicle‐miles travelled). Incremental designs were carried out and cost functions were developed using Association of State Highway and Transportation Officials’ (AASHTO) design vehicles. Each Federal Highway Administration (FHWA) vehicle weight group was classified into an equivalent AASHTO loading regime using the modified equivalent vehicle (MEV) model which is based on gross vehicle weight, axle loading and axle spacing. The results were used to incrementally assign bridge cost to each vehicle class. For each class of overweight vehicles, the bridge damage cost was computed as the ratio of the cost responsibility and the volume of these vehicles. The bridge damage cost was estimated under two permit fee options and three user charging scenarios. The results suggest that approximately 22% of total bridge cost can be considered attributable to overweight vehicles. Also, it was observed that the bridge damage cost is not just a factor of gross vehicle weight but a function of all the three vehicle‐related variables: gross vehicle weight, axle spacing and axle loads. It was concluded that the adoption of a permit structure on the basis of gross vehicle weight only, will result in certain vehicle classes underpaying by as much as 92% of their actual contribution to bridge damage. Finally, the study examined cost and operational issues associated with the enforcement of overweight truck policies and identified a number of locations that could be considered for establishing new weigh stations and other enforcement facilities.