The reliability of cutting tools is critical to machining precision and production efficiency. The conventional statistic-based reliability assessment method aims at providing a general and overall estimation of reliability for a large population of identical units under given and fixed conditions. However, it has limited effectiveness in depicting the operational characteristics of a cutting tool. To overcome this limitation, this paper proposes an approach to assess the operation reliability of cutting tools. A proportional covariate model is introduced to construct the relationship between operation reliability and condition monitoring information. The wavelet packet transform and an improved distance evaluation technique are used to extract sensitive features from vibration signals, and a covariate function is constructed based on the proportional covariate model. Ultimately, the failure rate function of the cutting tool being assessed is calculated using the baseline covariate function obtained from a small sample of historical data. Experimental results and a comparative study show that the proposed method is effective for assessing the operation reliability of cutting tools.