Microdrilling is one of the most difficult operations because of the poor chip discharge and the weakness of tool. This study is concerned about the development of a microdrilling monitoring system that is useful for minimizing the tool breakage and enhancing the machinability in the air spindle based microdrilling. The system is composed of a drilling state detection unit and an adaptive step-feed control unit that controls the micro-stepping motor driven spindle axis. Drilling states such as overload, tood breakage are recognized by the change of the air spindle speed which is measured via the reflective photo sensor. Based on the monitoring results, the adaptive step-feed control algorithm adjusts the step increment to keep the decrease of spindle speed within a specified range. The results of evaluation tests have shown that the developed system is very effective to prevent the breakage of microdrill and improves the productivity in comparison with the conventional microdrilling.