As electronic devices continue to shrink in size and increase in functionality, effective thermal management has become a critical bottleneck that hinders continued advancement. Two-phase cooling technologies are of growing interest for electronics cooling due to their high heat removal capacity and small thermal resistance (<0.1 k cm2/W). One typical example of a two-phase cooling method is droplet evaporation, which can provide a high heat transfer coefficient with low superheat. While droplet evaporation has been studied extensively and used in many practical cooling applications (e.g.,, spray cooling), the relevant work has been confined to spherical droplets with axisymmetric geometries. A rationally designed evaporation platform that yields asymmetric meniscus droplets can potentially achieve larger meniscus curvatures, which gives rise to higher vapor concentration gradients along the contact line region, and therefore, yields higher evaporation rates. In this study, we develop a numerical model to investigate the evaporation behavior of asymmetrical microdroplets suspended on a porous micropillar structure. The equilibrium profiles and mass transport characteristics of droplets with circular, triangular, and square contact shapes are explored using the volume of fluid (VOF) method. The evaporative mass transport at the liquid–vapor interface is modeled using a simplified Schrage model. The results show highly nonuniform mass transport characteristics for asymmetrical microdroplets, where a higher local evaporation rate is observed near the locations where the meniscus has high curvature. This phenomenon is attributed to a higher local vapor concentration gradient that drives faster vapor diffusion at more curved regions, similar to a lightning rod exhibiting a strong electric field along a highly curved surface. By using contact line confinement to artificially tune the droplet into a more curved geometry, we find that the total evaporation rate from a triangular-based droplet is enhanced by 13% compared to a spherical droplet with the same perimeter and liquid–vapor interfacial area. Such a finding can guide the design and optimization of geometric features to improve evaporation in advanced microcooling devices.