This study provides, to the best of our knowledge, the first detailed analysis of how surface oil modifies air–sea interactions in a two-way coupled model, i.e., the coupled–ocean–atmosphere–wave–sediment–transport (COAWST) model, modified to account for oil-related changes in 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 (20 April to 5 May 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 were treated as being unchanged by oil, the surface stress changes were always negative because of oil-related dampening of the surface roughness alone. However, the oil-related changes to 10 m wind speeds and boundary-layer stability were 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 were due to oil-related changes in wind speed and boundary-layer stability. Finally, the oil-related changes in surface stress due to the combined oil-related changes in surface roughness, surface wind, and boundary-layer stability were not large enough to have a major impact on the surface current and surface oil transport, indicating that the feedback from the surface oil to the surface oil movement itself is insignificant in forecasting surface oil transport unless the fractional oil coverage is much larger than the value found in this study.