The Kuroshio Extension (KE) fluctuates between its different dynamic regimes on (quasi) decadal time scales. In its stable (unstable) regime, the KE jet is strengthened (weakened) and less (more) meandering. The present study investigates wintertime mesoscale atmospheric structures modulated under the changing KE regimes, as revealed in high-resolution satellite data and data from a particular atmospheric reanalysis (ERAInterim). In the unstable KE regime, a positive anomaly in sea surface temperature (SST) to the north of the climatological KE jet accompanies positive anomalies in upward heat fluxes from the ocean, surface wind convergence, and cloudiness. As revealed in the atmospheric reanalysis, these positive anomalies coincide with local lowering of sea level pressure, weaker vertical wind shear, warming and thickening of the marine atmospheric boundary layer (MABL), anomalous ascent, and convective precipitation. In the stable KE regime, by contrast, the corresponding imprints of sharp SST gradients across the KE and Oyashio fronts on the wintertime MABL are separated more distinctly, and so are the surface baroclinic zones along those two SST fronts. In the ERA-Interim data, such mesoscale imprints of the KE variability as above are not well represented in a period during which the resolution of SST data prescribed is relatively low. The present study thus elucidates the importance of high-resolution SST data prescribed for atmospheric reanalysis in representing modulations of the MABL structure and air-sea fluxes by the variability of oceanic fronts and/or jets, including the modulations occurring with the changing KE regimes through the hydrostatic pressure adjustment and vertical mixing mechanisms.