In this study, we use observations and the Weather Research and Forecasting (WRF) model to investigate the tropical storm structure and storm environment, the effect of Dominica's orography, and other aspects that played a role in the heavy precipitation. Preliminary results show that the large-scale vertical wind shear was a key factor in organizing convection southeast of the low-level center of circulation. However, other mesoscale factors were also influential, as both observations and the WRF simulations show channelling flow and convergence between Dominica and Martinique. WRF simulations with reduced terrain have reduced rainfall suggesting that interactions between the storm winds and Dominica’s orography contributed to the heavy precipitation. Our results highlight the multi-scale interactions that can contribute to heavy precipitation associated with tropical cyclone passage near mountainous islands.