Tropical convection during the onset of two Madden-Julian oscillation (MJO) events, in October and December of 2011, was simulated using the Weather Research and Forecasting (WRF) Model. Observations from the Dynamics of the MJO (DYNAMO) field campaign were assimilated into the WRF Model for an improved simulation of the mesoscale features of tropical convection. The WRF simulations with the assimilation of DYNAMO data produced realistic representations of mesoscale convection related to westerly wind bursts (WWBs) as well as downdraft-induced gust fronts. An end-to-end simulator (E2ES) for the Cyclone Global Navigation Satellite System (CYGNSS) mission was then applied to the WRF dataset, producing simulated CYGNSS near-surface wind speed data. The results indicated that CYGNSS could detect mesoscale wind features such as WWBs and gust fronts even in the presence of simulated heavy precipitation. This study has two primary conclusions as a consequence: 1) satellite simulators could be used to examine a mission's capabilities for accomplishing secondary tasks and 2) CYGNSS likely will provide benefits to future tropical oceanic field campaigns that should be considered during their planning processes.