Abstract Idealized large-eddy simulations (LESs) with prescribed heterogeneous land surface heat fluxes are performed to study the impact of the heterogeneity length scale and background wind speed on the development of shallow cumulus and the subsequent transition to congestus/deep convection. We study the impact of land surface heterogeneity in an atmosphere that favors shallow convection but is also conditionally unstable with respect to deeper convection. We find that before the convection transition, larger and thicker shallow cumulus clouds are attached to moisture pools near the PBL top over patches with low evaporative fraction (referred to as “DRY”). This feature is attributable to a surface-induced secondary circulation whose development depends on the heterogeneity size and the background wind speed. With large patches (≥5 km) under zero ambient wind, the secondary mesoscale circulation promotes the vertical transport of moisture forming a moisture pool over DRY patches, while with smaller patches, no such circulation develops. The influence of the background wind on the secondary circulation is strong such that any wind stronger than 2 m s−1 effectively eliminates the impact of surface heterogeneity on the PBL and brings no secondary circulation. This is because the triggered secondary circulation is not strong enough to withstand the imposed background wind. Based on these, we propose two criteria for the convection transition, namely, that the heterogeneity length scale is greater than 5 km and that the background wind speed is less than Uc0, where Uc0 is the near-surface cross-patch wind speed of the secondary circulation under zero background wind for a given patch size and is about 1.5 m s−1 in our cases.