High-resolution numerical simulations of the Adriatic Sea using the Navy Coastal Ocean Model (NCOM) and Coupled Ocean–Atmosphere Mesoscale Prediction System (COAMPS) were conducted to examine the impact of the coupling strategy (one versus two way) on the ocean and atmosphere model skill, and to elucidate dynamical aspects of the coupled response. Simulations for 23 September–23 October 2002 utilized 2- and 4-km resolution grids for the ocean and atmosphere, respectively. During a strong wind and sea surface cooling event, cold water fringed the west and north coasts in the two-way coupled simulation (where the atmosphere interacted with SST generated by the ocean model) and attenuated by approximately 20% of the cross-basin extension of bora-driven upward heat fluxes relative to the one-way coupled simulation (where the atmosphere model was not influenced by the ocean model). An assessment of model results using remotely sensed and in situ measurements of ocean temperature along with overwater and coastal wind observations showed enhanced skill in the two-way coupled model. In particular, the two-way coupled model produced spatially complex SSTs after the cooling event that compared more favorably (using mean bias and rms error) with satellite multichannel SST (MCSST) and had a stabilizing effect on the atmosphere. As a consequence, mean mixing was suppressed by over 20% in the atmospheric boundary layer and more realistic mean 10-m wind speeds were produced during the monthlong two-way coupled simulation.