This chapter discusses classification, geometry, and design of deep-hole drills. The concept of self-piloting is explained. The system approach to deep-hole machining is introduced and common system issues are discussed with examples. The major emphasis is placed on gundrills. A number of simple design rules are proposed and explained with examples. The conditions of free penetration of the drill into the hole being drilled are explained. The geometry consideration is systemically related to MWF flow and thus the concept of the optimum MWF flow rate is explained. A number of novel design concepts are revealed. This chapter also discusses system consideration in experimental study of gundrill parameters. It is demonstrated that tool life is a complex function not only of geometry parameters and machining regime alone but also of their combination. Tool geometry optimization using the Hooke and Jeeves method is also discussed.