This study introduces a new tool breakage detecting technology comprised of an unsupervised neural network combined with adaptive time series autoregressive(AR) model where parameters are estimated recursively at each sampling instant using a parameter adaptation algorithm based on an RLS(Recursive Least Square). Experiment indicates that AR parameters are good features for tool breakage, therefore it can be detected by tracking the evolution of the AR parameters during milling process. an ART 2(Adaptive Resonance Theory 2) neural network is used for clustering of tool states using these parameters and the network is capable of self organizing without supervised learning. This system operates successfully under the wide range of cutting conditions without a priori knowledge of the process, with fast monitoring time.