Purpose: Excessive drill advancement after cortical breakthrough is a potential safety concern in orthopaedic procedures. We developed a data-driven approach to estimate the drill-tip position relative to the far cortex prior to breakthrough using time-series thrust force and spindle torque signals. Methods: Drilling experiments were performed on 268 porcine cortical bone specimens at a constant feed rate of 0.5 mm/s. A long short-term memory network was trained to estimate the drill-tip position from filtered force and torque signals. The reference position was derived from breakthrough timing confirmed by high-speed imaging and the programmed feed rate. Performance was evaluated using mean absolute error within the −2 to +2 mm peri-breakthrough interval. Two post hoc analyses examined whether model performance exceeded an elapsed-time baseline and whether pre-breakthrough force patterns were more consistent when expressed relative to breakthrough position than to drilling onset time. Results: The combined-input LSTM achieved an MAE of 0.20 mm, compared with 0.23 mm for force alone and 0.24 mm for torque alone. Among the representative architectures evaluated, LSTM showed the lowest regression error. A signal-blind time-only baseline yielded an MAE of 0.54 mm. The association between cortical thickness and force-decline onset was weaker when expressed in spatial coordinates relative to breakthrough than when expressed as time from drilling onset (R² = 23% vs. 74%). These findings suggest that force and torque signals contained information associated with proximity to breakthrough beyond that provided by average drilling duration alone. Conclusion: Converting sensor-derived resistance patterns into spatially anchored positional information may support proactive strategies such as controlled deceleration before penetration. The proposed approach represents a step toward exemplifying the emerging concept of surgeon-assisting Physical AI.