Observations of ocean–atmosphere coupling across persistent mesoscale sea surface temperature (SST) gradients are used to examine the controls of atmospheric stability, pressure gradient force, and heat flux that are considered central to oft-observed coupling between wind and SST. Moored air–sea flux measurements near the Gulf Stream are combined with QuikSCAT satellite scatterometer equivalent neutral wind (ENW) data to assess correlations between SST, air–sea fluxes, pressure, and wind perturbations at scales of 10–100 days. The net effect of ocean fronts meandering past the site enabled buoy observation of SST impacts on wind, with coupling coefficients of 0.3–0.5 similar to past studies. Wind stress–SST and ENW–SST correlation coefficients are slightly higher, and roughly 20% of the ENW perturbation is attributed to stratification impacts predicted by Monin–Obukhov (MO) similarity theory. Significantly higher correlation is observed when relating wind or stress perturbations to buoyant heat flux variation. Atmospheric pressure perturbation with SST of order 0.5 hPa °C−1 is observed, as well as high negative correlation between wind and pressure variations. Length and time scales associated with the coupling indicate that peak correlations occur at 50–70 days and 300–500 km, consistent with mesoscale meander scales. Coupling coefficient values vary significantly depending on analysis time scale and exhibit a range near to recently observed interbasin variability. This variability is attributed to the extent of oceanic length scales permitted in the analysis. Together, results affirm the central role of SST-induced turbulent heat flux in controlling pressure field adjustments and thereby the wind perturbations over SST fronts.