This study examines how organized lines of deep convective storms can be impacted by a large city with a prominent urban heat island and how low‐level environmental vertical wind shear may influence the outcomes of that interaction. Idealized simulations of squall lines are conducted in which a simplified urban area—defined by perturbations to skin temperature and surface roughness length—is placed in the center of an otherwise horizontally homogeneous domain. Simulations are conducted with three different magnitudes of low‐level vertical wind shear representing “weak,” “medium,” and “strong” shear environments. Results show that storms experience noticeable modification—including enhanced downwind precipitation—after interacting with a prominent urban heat island in all three shear configurations. However, the details of the modification are a function of the shear magnitude. In the medium and strong shear simulations, updrafts are enhanced via increased buoyancy after passing over a prominent urban heat island. In contrast, little updraft strengthening is evident in the weak‐shear simulations. Instead, near‐surface winds are enhanced downwind of the urban heat island due to a more prominent descending rear‐inflow jet.