Tool condition monitoring is difficult in micro-milling due to irregular wear and chipping of the cutting edges, which lead to unexpected tool breakage. This study demonstrates the use of force data to reliably predict different tool life stages until tool breakage, while micro-milling hard materials like stainless steel (SS304) using tungsten carbide tools of 500 μm diameter. Extensive experiments involving machining of 465 slots over 62 min of machining time were performed in this study. The resulting voluminous force data were analyzed to divide the tool life into three stages based on the variation in the forces and other related features. The first stage is the initial 12.5% of the tool life, second stage consists of 12.5–70% of tool life, and the third stage is from 70% to 100% tool life. The analysis of the tool wear and cutting forces shows that the average tool diameter reduces by 32 μm, 67 μm and 108 μm, and the average resultant cutting force were 2.45 N, 4.17 N, and 4.93 N in stage 1, 2, and 3, respectively. To avoid catastrophic breakage of the tool, the tool life stages are predicted from the force data using machine learning models. Among the machine learning models, random forest method gave a better prediction accuracy of 88.5%. The model was further improved by incorporating the initial cutting edge radius as an additional feature, and the variance in the prediction was seen to drop by 48.76%.