We present a comprehensive analysis of the imaging characteristics of a scanning microwave microscopy (SMM) system operated in the transmission mode. In particular, we use rigorous three-dimensional finite-element simulations to investigate the effect of varying the permittivity and depth of sub-surface constituents of samples, on the scattering parameters of probes made of a metallic nano-tip attached to a cantilever. Our results prove that one can achieve enhanced imaging sensitivity in the transmission mode SMM (TM-SMM) configuration, from twofold to as much as 5× increase, as compared to that attainable in the widely used reflection mode SMM operation. In addition, we demonstrate that the phase of the S 21-parameter is much more sensitive to changes of the system parameters as compared to its magnitude, the scattering parameters being affected the most by variations in the conductivity of the …