The proposed transition to single-pilot operations (SPO) in commercial and military aircraft has motivated the development of advanced autonomy systems. However, a detailed analysis of the impact of advanced autonomy on pilot workload through various phases of flight and contingency scenarios has not been conducted. To this end, this paper presents the development of the Pilot-Autonomy Workload Simulation (PAWS), a discrete event simulation model that allows the investigation of pilot workload under a variety of advanced autonomy capabilities and scenarios. Initial utilization results from PAWS of nominal and offnominal point-to-point missions demonstrate that the workload for a single pilot assisted by advanced autonomy varies considerably over different phases of flight and various contingencies. These results suggest that advanced autonomy to offset pilot workload is not needed for low-workload phases, but could be critical during periods of high workload.