The paper develops a set of analytical formulations to study the behavior of the urban delivery industry in response to cordon time-of-day pricing, time–distance pricing, and comprehensive financial policies targeting carriers and receivers. This is accomplished by modeling the behavior of receivers in response to financial incentives, and the ensuing behavior of the carrier in response to both pricing and the receivers’ decisions concerning off-hour deliveries. The analytical formulations consider both the base case condition, and a mixed operation with both regular hour and off-hour deliveries; two pricing schemes: cordon time of day, and time–distance pricing; two types of operations: single-tour, and multi-tour carriers; and three different scenarios in terms of profitability of the carrier operation, which include an approximation to the best case, the expected value, and the worst case. The analyses, both theoretical and numerical, highlight the limitations of pricing-only approaches. In the case of cordon time of day pricing, the chief conclusion is that it is of limited use as a freight demand management tool because: (1) in a competitive market the cordon toll cannot be transferred to the receivers as it is a fixed cost and (2) the structure of the cost function, that only provides an incentive to the carrier to switch to the off-hours when all the receivers in the tour switch to the off-hours. The analyses of time–distance pricing clearly indicate that, though its tolls could be transferred to the receivers and provide an incentive for behavior change, the magnitude of the expected toll transfers under real life conditions are too small to have any meaningful impact on receivers choice of delivery times. In essence, the key policy implication is that in order to change the joint behavior of carrier and receivers, financial incentives—or programs that foster unassisted off-hour deliveries—should be made available to receivers in exchange for their commitment to do off-hour deliveries. As the paper proves, if a meaningful number of receivers switch to the off-hours, the carriers are likely to follow suit.