This study provides, to our knowledge, the first detailed analysis of how surface oil modifies air-sea interaction in a two-way coupled model, i.e., the coupled-ocean-atmosphere-wave-sediment-transport (COAWST) model modified to account for oil-related changes to air-sea fluxes. This study investigates the effects of oil on surface roughness, surface wind, surface and near surface temperature differences, and boundary-layer stability, and how those conditions ultimately affect surface stress. We first conducted twin coupled modeling simulations with and without the influence of oil over the Deepwater Horizon (DWH) oil spill period (April 21 to May 5, 2010) in the Gulf of Mexico. Then we compared the results by using a modularized flux model with parameterizations selected to match those selected in the coupled model adapted to either ignore or account for different atmospheric/oceanic processes in calculating surface stress. When non-oil inputs to the bulk formula treated as unchanged by oil, the surface stress changes are always negative due to oil-related damping of surface roughness alone. However, the oil-related changes to 10-m wind speed and boundary-layer stability are found to play a dominant role in surface stress changes relative to those due to the oil-related surface roughness changes, highlighting that most of the changes in surface stress are due to the oil-related changes in wind speed and boundary-layer stability. Finally, the oil-related changes to surface stress due to the combined oil-related changes in surface roughness, surface wind, and boundary-layer stability are not large enough to have a major impact on the surface current and surface oil transport, indicating that the feedbacks from the surface oil to the surface oil movement itself are minor for forecasting the surface oil transport unless the fractional oil coverage is much larger than found in this study.