Hurricane Maria drastically altered the landscape across the island of Puerto Rico. This article investigates modifications to surface-atmospheric interactions due to Hurricane Maria induced land damage and the associated impacts on local convective dynamics. Herein, we employed LANDSAT-8 image mosaics to quantify the hurricane induced land modification. Results of the analysis indicate that the island suffered significant forest damage—much of which registered as a 28.35% increase in barren land and a 10.85% increase in pasture. Smaller changes included a decrease in cultivated agricultural land cover by 0.76%, along with wetland and water increases of 0.62% and 0.25%, respectively. Pre and post-Maria land classifications were then assimilated into the Regional Atmospheric Modeling System cloud resolving model for the simulation of the June 23 to July 2, 2018 period under two land conditions. Results of the numerical experiments indicate that surface to atmosphere interactions were significantly modified when the land cover was altered, and that the highest deviations between pre- and post-Maria convection occurred over elevated areas with extreme hurricane induced land changes, such as the Cordillera Central mountain range and the El Yunque rainforest.