Detecting anomalies such as breakage and excessive wear of cutting tools in the machining process is crucial to prevent damage and improve productivity. Data-driven anomaly detection (AD) methods suffer from limited availability of anomaly samples, which is ineluctable in practice owing to strict reliability restrictions. Therefore, we propose a semisupervised AD approach in which only failure-free samples are required to establish an AD model. The key strategy is to learn the characteristics of failure-free samples using an improved autoencoder (AE) and discern observations by deviations from the characteristics. We rebuild the loss function of AE to impel the model to learn the common characteristics in latent space. We propose a factor that reflects the anomaly degree as the decision-making function to implement AD. The proposed approach is verified on an experimental cutting tool breakage dataset and a public cutting tool wear dataset. The experimental results demonstrate the validity of the proposed approach. The comparisons with conventional methods substantiate that the proposed approach outperforms existing AD methods.