We use the mountainous Caribbean island of Dominica to investigate the downslope winds that occur in a moist, convecting, trade wind flow. Airborne in-situ and dual-Doppler cloud radar measurements taken during the DOMEX-2011 field campaign are used to characterize the plunging, turbulent, warm, and dry flow that often occurs over Dominica's lee slopes. This flow bears many similarities to mid-latitude downslope winds and hydraulic analogs, despite the presence of vigorous moist convection and substantial latent heat release over the windward slopes. High-resolution numerical simulations with the WRF model are used to determine how various environmental conditions (incoming flow speed, inversion structure, mean-state critical layers) and processes (latent heating, moist convection) control the strength and structure of Dominica's downslope winds.