The design of topological features to control the spreading of liquid has been widely investigated. Micropillar structures, for example, can retain stable droplets on the tip by inhibiting the contact line from advancing over a sharp solid edge. The pinning behavior of droplets on noncircular pillars, however, has received little attention. In this study, we analyze the retention of microdroplets with high and low surface tensions on axisymmetric and asymmetric porous micropillar structures. Circular, square, and triangular structures fabricated on silicon substrates are used to characterize the dynamic behavior of droplets before and after bursting. The critical pinning conditions are based on the visualization and pressure measurements of droplets. A theoretical model is developed based on a free energy analysis for predicting the change in pressure as the working fluid advances on the micropillar. For high surface tension liquids (e.g., water), the maximum pressure occurs when the contact line is pinned along the edge of the inner pore. For low surface tension liquids (e.g., Isopropanol and Novec 7500), the maximum pressure occurs when the contact line is pinned along the outer edge of the structure. The theoretical and experimental results demonstrate how a droplet pinned atop a triangular micropillar exhibits the smallest critical volume at the bursting moment. When using IPA solution (γ = 23 mN/m) and Novec 7500 (γ = 16 mN/m) as the working fluids, a change in the micropillar shape from circle to triangle, respectively, yields a 83% and 76% reduction in the critical burst volume. Meanwhile, the bursting pressure increases from 172 to 300 Pa and from 127 to 216 Pa for IPA and Novec 7500, respectively. These findings provide new insights to the rational design of surface micro/nanoengineered structures for tuning the surface wetting characteristics in scientific and engineering applications.