Upper tropospheric stratiform clouds associated with deep convection are important to global radiation budgets and to cloud-radiation feedbacks on climate variability and change. Several recent observational studies indicate that vertical wind shear is an important factor affecting stratiform cloud fraction and cloud overlap. This study further examines wind shear effects on cloud properties (including cloud fraction and cloud optical depth) and associated top of atmosphere (TOA) and surface radiative fluxes, using observations from the Tropical Ocean Global Atmosphere program's Coupled Ocean Atmosphere Response Experiment (TOGA COARE) experiment and long-term satellite measurements. Wind shear affects cloud-radiative fluxes, through both the cloud fraction and optical thickness, in a strong and systematic way. In typical convecting conditions, shear-induced additional cloudiness can reduce outgoing longwave radiation (OLR) by 10s of Wm-2, implying longwave radiative changes on the order of 10% of the total latent heating. Such cloud also reflects shortwave radiation, reducing surface downward flux (energy input to the ocean) by 10s of Wm-2. Current climate models lack these effects.