Lubricant-infused surfaces (LISs) can promote stable dropwise condensation and improve heat transfer rates due to a low nucleation free-energy barrier and high droplet mobility. Recent studies showed that oil menisci surrounding condensate microdroplets form distinct oil-rich and oil-poor regions. These topographical differences in the oil surface cause water microdroplets to rigorously self-propel long distances, continuously redistributing the oil film and potentially refreshing the surface for re-nucleation. However, the dynamic interplay between oil film redistribution, microdroplet self-propulsion, and droplet nucleation and growth is not yet understood. Using high-speed microscopy, we reveal that during water condensation on LISs, the smallest visible droplets (diameter: ∼1 μm, qualitatively representing nucleation) predominantly emerge in oil-poor regions due to a lower nucleation free-energy barrier. Considering the significant heat transfer performance of microdroplets (<10 μm) and transient characteristic of microdroplet movement, we compare the apparent nucleation rate density and water collection rate for LISs with oils of different viscosities and a solid hydrophobic surface at a wide range of subcooling temperatures. Generally, the lowest lubricant viscosity leads to the highest nucleation rate density. We characterize the length and frequency of microdroplet movement and attribute the nucleation enhancement primarily to higher droplet mobility and surface refreshing frequency. Interestingly and unexpectedly, hydrophobic surfaces outperform high-viscosity LISs at high subcooling temperatures but are generally inferior to any of the tested LISs at low temperature differences. To explain the observed nonlinearity between LISs and the solid hydrophobic surface, we introduce two dominant regimes that influence the condensation efficiency: mobility-limited and coalescence-limited. We compare these regimes based on droplet growth rates and water collection rates on the different surfaces. Our findings advance the understanding of dynamic water–lubricant interactions and provide new design rationales for choosing surfaces for enhanced dropwise condensation and water collection efficiencies.