Self-propelled jumping of condensate droplets (dew) enables their easy and efficient removal from surfaces and is essential for enhancing the condensation heat transfer coefficient and for delaying the frost growth rate on supercooled surfaces. Here, we report the droplet-jumping phenomenon using nanoporous vertically aligned carbon nanotube (VA-CNT) microstructures grown on smooth silicon substrates and coated with poly-(1H, 1H, 2H, 2H-perfluorodecylacrylate) (pPFDA). We also report droplet-sweeping phenomenon on horizontally mounted surfaces, concluding that the frost surface coverage area and the frost growth rates observed with the droplet-sweeping phenomenon are much lower than those that are observed with the droplet-jumping phenomenon alone. We also investigate the fundamentals of droplet-jumping and the frost growth phenomena using line-shaped, hollow-cylindrical, and cylindrical microstructures, comparing the frost surface coverage area and the ice-bridging times during condensation-frosting, prolonged condensation-frosting, and direct-frosting. We find that the closely spaced thin line-shaped microstructures and hollow-cylindrical microstructures are optimal for frost coverage reduction because of their ability to exhibit droplet-jumping and droplet-sweeping phenomena. We observe that adding nonuniform roughness on top of the microstructures leads to jumping-associated droplet-sweeping on supercooled surfaces. Here, we report the evaporation of an already frozen droplet because of freezing of a supercooled condensate droplet in its close vicinity, enabling the Cassie–Baxter state frost growth and enhancing defrosting efficiency. Finally, we discuss the dynamic defrosting behavior of the pPFDA-coated VA-CNT microstructures, concluding that the small gaps (spacings) between the microstructures not only enable dewetting transitions of droplets but also promote the Cassie–Baxter state frost formation.