Growing numbers of decision makers are becoming more open to charging users of roads to fund transportation improvements, including transit alternatives. Despite significant progress, planners and policy makers still face many obstacles when considering road-pricing projects. This suggests that many of the factors that determine the success or failure of such proposed projects are not well understood and that proposed projects may include one or more aspects that prove to be deal breakers for key supporters. Four geographically diverse California road-pricing projects were selected for detailed case studies. Two projects that succeeded to implementation allow for an analysis of the critical political maneuvers made throughout the life of these priced facilities. One project that was ultimately halted in the later stages of planning and one planned but not yet implemented project are useful in evaluating what went wrong and what lessons can be drawn from these attempts to implement road pricing. The findings suggest that there are numerous ways to adjust pricing projects to gain public and political support. Generally, projects should try to provide more capacity, travel-time savings, and travel options, and avoid pricing facilities that have no free alternatives. Nevertheless, the manner in which projects are designated and revenues are used is highly context-specific, and some concessions in one area can improve acceptability in another. The future of road pricing is uncertain, and pricing projects should be considered only on a case-by-case basis, depending on local attitudes, the use of the revenue generated, and the specific facility in question.