This paper is aimed at gaining a better understanding of how to increase participation in off-hour deliveries by using behavioral microsimulation (BMS) of carrier-receiver interactions. BMS is used to study the effectiveness of policies such as time-of-day pricing and financial incentives to receivers in exchange for their acceptance of off-hour deliveries. The main components of this BMS are the simulations of receiver and carrier behaviors. The simulation of receiver behavior uses a discrete choice model to estimate receivers' decisions to accept or reject off-hour deliveries. The simulation of carriers' behaviors uses receivers' decisions as an input for deciding whether to make off-hour deliveries along with a computation of the associated delivery costs. The analyses done revealed several key results: (a) tax deductions given to receivers in exchange for accepting off-hour deliveries and financial rewards to carriers making off-hour deliveries would increase participation in off-hour deliveries, (b) time-of-day toll surcharges have no major impact on increasing off-hour deliveries, (c) carriers located close to their urban customers are more likely to participate in off-hour deliveries because they can easily start to accrue the benefits from off-hour delivery operations, and (d) increased enforcement of parking fines for double-parking during regular hours could increase the number of carriers participating in off-hour deliveries.