Direct milling of sand molds is an important development in rapid manufacturing of sand molds. Direct milling is an effective method for manufacturing single or small batches of cast parts. This paper describes experimental investigations to find sand blocks with the appropriate strength, to describe wear patterns of different tools (high-speed steel (HSS), carbide, and polycrystalline diamond (PCD) tools), and to analyze sand mold cutting mechanisms. The results show that the PCD tool outperformes the other tools in terms of tool life. Average flank wear and micro-tipping are the dominant tool failure modes in the sand mold milling process. With a flank wear limit of 0.3 mm, the PCD tool works continuously for about 70 h under the experimental conditions. The experimental results show that the cutting mechanism for direct milling sand molds differs from metal cutting.