Lowering droplet–surface interactions via the implementation of lubricant-infused surfaces (LISs) has received important attention in the past years. LISs offer enhanced droplet mobility with low sliding angles and the recently reported slippery Wenzel state, among others, empowered by the presence of the lubricant infused in between the structures, which eventually minimizes the direct interactions between liquid droplets and LISs. Current strategies to increase heat transfer during condensation phase-change relay on minimizing the thickness of the coating as well as enhancing condensate shedding. While further surface structuring may impose an additional heat transfer resistance, the presence of micro-structures eventually reduces the effective condensate–surface intimate interactions with the consequently decreased adhesion and enhanced shedding performance, which is investigated in this work. This is demonstrated by macroscopic and optical microscopy condensation experimental observations paying special attention at the liquid–lubricant and liquid–solid binary interactions at the droplet–LIS interface, which is further supported by a revisited force balance at the droplet triple contact line. Moreover, the occurrence of a condensation–coalescence–shedding regime is quantified for the first time with droplet growth rates one and two orders of magnitude greater than during condensation–coalescence and direct condensation regimes, respectively. Findings presented here are of great importance for the effective design and implementation of LISs via surface structure endowing accurate droplet mobility and control for applications such as anti-icing, self-cleaning, water harvesting, and/or liquid repellent surfaces as well as for condensation heat transfer.