Unexpected drill breakage can be foreseen and prevented. We observed a factory and identified the warning signs of tool breakage for micro gundrills, as well as a laboratory experiment for micro drills. The vibrations of stable drilling and the vibrations that warn of tool breakage were analyzed based on the time and frequency domain features. We developed a prognostic model. We conducted physical drilling experiments on a Swiss turning machine and a laboratory research platform. Stainless steel was drilled with two types of 0.9-mm-diameter tools: 125-mm-long micro gundrills on Swiss turning machine and 25-mm-long micro drills. In both types of testing, two accelerometers were installed on the tool holder to collect two-directional vibration signals; a linear discriminant function processed the Z-axis and Y-axis signals for the telltale warning signs of impending tool breakage, and obtained a 100% classification rate. To confirm the effect of drilling disturbances on the prognostic system, the entries and exits of tools to and from workpieces were studied. The results demonstrate that both types of signal features can be used without causing any misclassification.