Time-access regulations and vehicle restrictions are increasingly used, especially in western Europe, to improve social sustainability in urban areas. These regulations considerably affect the distribution process of retail chain organizations as well as the environmental burden. This paper studies the impact of governmental time windows, vehicle restrictions, and different retailers' logistical concepts on the financial and environmental performance of retailers. We use a case study with two cases that differ in their drop sizes as input for an experiment. The retailers provided all organizational, flow, and cost data of the distribution process between their distribution centers and their stores. We use these data to calculate the impacts of different scenarios on the retailers' financial and environmental performances based on a fractional factorial design in which urban policies and the retailers' logistical concepts are varied, using vehicle routing software. We test the propositions with a third case. We show that the cost impact of time windows is the largest for retailers who combine many deliveries in one vehicle round-trip. The cost increase due to vehicle restrictions is the largest for retailers whose round-trip lengths are restricted by vehicle capacity. Vehicle restrictions and time windows together do not increase a retailer's cost more than individually. Variations in delivery volume and store dispersion hardly influence the impact of urban policy and the retailer's logistical concept decisions. © 2009 INFORMS.