Using cutting fluids is considered in industrial applications and academia due to their increased influence over many aspects such as machinability, sustainability and manufacturing costs. This paper addresses the machinability perspective by examining indicators such as roughness, cutting temperature, tool wear and chip morphology during the milling of mold steel. A special type of steel is Nimaxm which is a difficult-to-cut material because of its high strength, toughness, hardness and wear resistance. Since mold steels have the reverse geometry of the components produced by this technology, their surface quality and dimensional accuracy are highly important. Therefore, two different strategies, i.e., dry and minimum quantity lubrication (MQL), were chosen to conduct an in-depth analysis of the milling performance during cutting at different cutting speeds, feed rates and cutting depths. Without exception, MQL technology showed a better performance than the dry condition in obtaining better surface roughnesses under different cutting parameters. Despite that only a small improvement was achieved in terms of cutting temperature, MQL was found to be successful in protecting the cutting tool from excessive amounts of wear and chips. This paper is anticipated to be a guide for manufacturers and researchers in the area of mold steels by presenting an analysis of the capabilities of sustainable machining methods.