Abstract The initiation of thunderstorms in environments characterized by strong wind shear presents a forecast challenge because of the complexities of the interactions between growing cumulus clouds and wind shear. Thunderstorms that develop in such environments are often capable of producing high-impact hazards, highlighting the importance of convection initiation in sheared environments. Although recent research has greatly improved understanding of the structure and evolution of rising thermals in unsheared environments, there remains uncertainty in how wind shear influences the convection initiation process. Two large-eddy simulations (75-m horizontal grid spacing) were performed to study this problem. Convection initiation attempts are forced in the simulations through prescribed surface heat fluxes (the initial boundary layers are statistically horizontally homogeneous and quasi–steady state but contain turbulent eddies as a result of random initial temperature perturbations). The only difference between the two simulations is the presence or absence of wind shear above 2 km. Important differences in the entrainment patterns are present between sheared and unsheared growing cumulus clouds. As found in previous research, the overturning circulation associated with rising thermals drives dynamic entrainment in the unsheared clouds. However, in sheared clouds, wake entrainment resulting from the tilting of environmental vorticity is an important dynamic entrainment pathway. This result has implications for both the structure of sheared growing cumulus clouds and for convection initiation in sheared environments. Significance Statement Forecasts of thunderstorm hazards such as tornadoes, hail, and strong winds, require the accurate prediction of when and where thunderstorms form. Unfortunately, predicting thunderstorm formation is not easy, as there are a lot of different factors to consider. One such factor is environmental vertical wind shear, which describes how winds change speed and direction with height. The purpose of this study is to better understand how wind shear impacts developing clouds. Our results demonstrate a specific mechanism, called “wake entrainment,” through which wind shear can weaken developing clouds and potentially prevent them from becoming strong thunderstorms entirely. Understanding this mechanism may be useful for thunderstorm prediction in environments characterized by wind shear.