The roadway infrastructure constantly deteriorates because of environmental conditions, but other factors such as exposure to heavy trucks exacerbates the rate of deterioration. Therefore, decision-makers are constantly searching for ways to optimize allocation of the limited funds for repair, maintenance, and rehabilitation of New Jersey’s infrastructure. New Jersey legislation requires operators of overweight (OW) trucks to obtain a permit to use the infrastructure. The New Jersey Department of Transportation (NJDOT) issues a variety of permits based on the types of goods carried. These permits allow OW trucks to use the infrastructure either for a single trip or for multiple trips. Therefore, one major concern is whether the permit revenue of the agency can recoup the actual cost of damage to the infrastructure caused by these OW trucks. This study investigates whether NJDOT’s current permit fee program can collect enough revenue to meet the actual cost of damage to the infrastructure caused by these heavy-weight permit trucks. The infrastructure damage is estimated by using pavement and bridge deterioration models and New Jersey permit data from 2013 to 2018 containing vehicle configuration and vehicle route. The analysis indicates that although the cost of infrastructure damage can be recovered for certain permit types, there is room for improvement in the permit program. Moreover, based on permit rules in other states, the overall rank of the New Jersey permit program is evaluated and possible revisions are recommended for future permit policies.