With the continuous growth in the number of motor vehicles in cities, “parking difficulty” has become a major issue restricting urban development. Promoting intelligent management and refined operation of on-street parking resources is a key path to improving public space utilization efficiency. Taking Pudong New Area of Shanghai as a case study, this paper systematically analyzes the mechanism of influence of three core factors—price, technology, and management—on vehicle owners’ parking behavior during the smart upgrading of on-street parking. The study finds that the smart upgrade significantly enhances the standardization of parking behavior and data transparency through means such as accurate charging, full-time supervision, and efficient overdue payment collection. However, in core areas with highly concentrated demand, the regulatory effect of the price leverage is relatively limited, and the demand factor remains dominant. This research provides empirical evidence and decision-making reference for optimizing urban parking management policies.