Strategies for obtaining deep slots in soft materials can vary significantly. Conventionally, the tool travels along the slot, removing material mainly with the side cutting edges. However, a “plunge milling” strategy is also possible, performing the cut vertically, taking advantage of the tip cutting edges that almost reach the center of the tool. Although both strategies are already commonly used, there is a clear gap in the literature in studies that compare tool wear, surface roughness, and productivity in each case. This paper describes an experimental study comparing the milling of deep slots in AA7050-T7451 aluminum alloy, coated with a novel DLCSiO500W3.5O2 layer to minimize the aluminum adhesion to the tool, using conventional and plunge milling strategies. The main novelty of this paper is to present a broad study regarding different factors involved in machining operations and comparing two distinct strategies using a novel tool coating in the milling of aeronautical aluminum alloy. Tool wear is correlated with the vibrations of the tools in each situation, the cycle time is compared between the cases studied, and the surface roughness of the machined surfaces is analyzed. This study concludes that the cycle time of plunge milling can be about 20% less than that of conventional milling procedures, favoring economic sustainability and modifying the wear observed on the tools. Plunge milling can increase productivity, does not increase tool tip wear, and avoids damaging the side edges of the tool, which can eventually be used for final finishing operations. Therefore, it can be said that the plunge milling strategy improves economic and environmental sustainability as it uses all the cutting edges of the tools in a more balanced way, with less global wear.