Abstract The response of boundary layer properties and cloudiness to changes in surface evaporative fraction (EF) is investigated in a single-column model to quantify the locally coupled impact of subgrid surface variations on the atmosphere during summer. Sensitive coupling days are defined when the model atmosphere exhibits large variations across a range of EFs centered on the analyzed value. Coupling sensitivity exists as both positive feedback (cloudiness increases with EF) and negative feedback (clouds increase with decreasing EF) regimes. The positive regime manifests in shallow convection situations, which are capped by a strengthened inversion and subsidence, restricting the vertical extent of convection to just above the boundary layer. Surfaces with larger EF (greater surface latent heat flux) can inject more moisture into the vertically confined system, lowering the cloud base and an increasing cloud liquid water path (LWP). Negative feedback regimes tend to manifest when large-scale deep convection, such as from mesoscale convective systems and fronts, is advected through the domain, where convection strengthens over surfaces with a lower EF (greater surface sensible heat flux). The invigoration of these systems by the land surface leads to an increase in LWP through strengthened updrafts and stronger coupling between the boundary layer and the free atmosphere. These results apply in the absence of heterogeneity-induced mesoscale circulations, providing a one-dimensional dynamical perspective on the effect of surface heterogeneity. This study provides a framework of intermediate complexity, lying between parcel theory and high-resolution coupled land–atmosphere modeling, and therefore isolates the relevant first-order processes in land–atmosphere interactions. Significance Statement Cloud formation, distribution, and other properties may be sensitive to heterogeneous surfaces depending on the strength and location of such heterogeneities and the background atmospheric state. This may drive differences in the cloud population depending on which part of the domain one is located. This may also lead to mesoscale circulations, which may strengthen or weaken this effect. Currently, climate models act on scales (∼100 km) that are too large to explicitly represent these processes, which are strongest at smaller scales (around 5–40 km). Therefore, subgrid-scale heterogeneity is neglected, and any predictability and model fidelity it may provide is lost. We use a simple model to diagnose sensitivity of the local atmosphere to surface variations meant to represent possible subgrid heterogeneity, providing a first-order estimate of its effect. We conclude that preferentially sensitive atmospheric states exist that lead to positive and/or negative feedback between land and atmosphere. This information is valuable to future climate model parameterizations aimed at improving the representation of these feedbacks.