In today’s manufacturing landscape, Digital Twins play a pivotal role in optimising processes and deriving actionable insights that extend beyond on-site calculations. These dynamic representations of systems demand real-time data on the actual state of machinery, rather than static images depicting idealized configurations. This paper presents a novel approach for monitoring tool and component wear in CNC milling machines by segmenting and classifying individual machining cycles. The method assumes recurring sequences, even with a batch size of 1, and considers a progressive increase in tool wear between cycles. The algorithms effectively segment and classify cycles based on path length, spindle speed and cycle duration. The tool condition index for each cycle is determined by considering all axis signals, with upper and lower thresholds established for quantifying tool conditions. The same approach is adapted to predict component wear progression in machine tools, ensuring robust condition determination. A percentage-based component state description is achieved by comparing it to the corresponding Tool Condition Codes (TCC) range. This method provides a four-class estimation of the component state. The approach has demonstrated robustness in various validation cases.