Abstract: This review paper explores the field of mesoscale to microscale modeling over complex terrain as it traverses multiple so-called gray zones. In an attempt to bridge the gap between previous large-scale and small-scale modeling efforts, atmospheric simulations are being run at an unprecedented range of resolutions. The gray zone is the range of grid resolutions where particular features are neither subgrid nor fully resolved, but rather are partially resolved. The definition of a gray zone depends strongly on the feature being represented and its relationship to the model resolution. This paper explores three gray zones relevant to simulations over complex terrain: turbulence, convection, and topography. Taken together, these may be referred to as the gray continuum. The focus is on horizontal grid resolutions from ∼10 km to ∼10 m. In each case, the challenges are presented together with recent progress in the literature. A common theme is to address cross-scale interaction and scale-awareness in parameterization schemes. How numerical models are designed to cross these gray zones is critical to complex terrain applications in numerical weather prediction, wind resource forecasting, and regional climate modeling, among others.