Since 2000, overloaded trucks have caused more than 50 bridges to collapse in China. In an effort to ensure the structural safety and extend the service life of the highway infrastructure, the Chinese government has proposed a series of policies in the past decade to mitigate truck overloading. This study aimed at investigating the effects of China’s recently revised toll-by-weight policy on truck overloading behavior and bridge infrastructure damage using weigh-in-motion data that spanned seven years (January 2011 to March 2018) and two successive toll-by-weight policies (with the new one implemented from August 2016), wherein truck data were measured from a typical national freeway segment. We first compared truck traffic volumes, compositions, and weight distributions under the initial and revised toll-by-weight policies. Next, we compared bridge infrastructure performance with respect to safety and fatigue based on the overloaded truck traffic observed under the initial and revised toll-by-weight policies. The results indicated that the revised toll-by-weight policy, which uses a stepwise incremental fee structure based on vehicle weight, was more effective at controlling truck overloading behavior and reducing bridge infrastructure damage than the initial toll-by-weight policy. Under the current policy, average daily truck volumes, overloaded truck proportions, and maximum truck weights decreased significantly. Concurrently, extreme and equivalent load effects for safety and fatigue assessments, respectively, decreased by an average of 20% for small- to medium-span bridges. Despite these noted improvements, overloaded truck traffic persisted, with loads often exceeding bridge design levels. This study’s findings can support future efforts by the Chinese government to further refine their toll-by-weight policies and subsequently ensure a safe and viable transportation network.