Within the paradigm of industry 5.0, manufacturing systems are seeking for human-centred production, where the operator finds high-level supervision tasks. In this context, low-level decision making should be performed by machines themselves. In this paper, a hybrid prognosis algorithm is developed to automatically inspect the cutting edges of drill-bits and to predict their Remaining Useful Life (RUL) and the associated probability density function. The solution relies on the automatic measurement of flank wear through convolutional filtering and edge detection. Prognosis exploits particle filter, which updates multi-layer perceptron with online data, to adaptively predict drill-bits RUL. The solution reduces the experimental preliminary run-to-failures needed for training standard machine learning algorithms, exploiting them in a real-time adaptive scenario, while predicting tool RUL under untested and variable cutting process operations. The algorithm uses direct wear observations, taken during set-up times (e.g., tool changes, workpiece change), thus not interfering with the process.