This chapter presents the most important features of high-penetration rate (HPR) drilling of high-silicon aluminum alloys (HSAA). It explains a necessity of implementation of HPR tools and well-designed machining operations that has become possible due to development of a number of new tool materials and coatings, new cutting inserts and tool designs, new tool holders, powerful precision machines, part fixtures, advanced controllers and so on. As the penetration rate is the product of the tool’s (workpiece) rotational speed and cutting feed, the major constraints of these two parameters are considered and a number of practical recommendation for increasing the penetration rate are made as the first level of the analysis. At the second level of the analysis, the correlations between the chemical composition and physical properties of HSAA and drilling tool/process parameters are explained. As HSAA are die casting alloys, the casting defect and their influence on tool performance are analyzed. It is pointed out that polycrystalline diamond (PCD) is a material of choice for HPR drilling tools for HSAA. The common problems with the existing PCD drilling tool are analyzed and the basic design of a cross-PCD drill is suggested.