Occupational stress in dentistry, particularly during endodontic procedures, impacts practitioners’ health and performance. This study introduces a novel approach using real-time Heart Rate (HR) data from Apple Watch technology to assess physiological responses potentially indicative of occupational stress among endodontists. Materials and Methods: Twelve endodontists participated in this study, treating 119 patients. In a controlled clinical environment, HR was continuously monitored with the Apple Watch, and data were recorded via the Cardiogram app, capturing HR variations across treatment stages. Results: Significant HR fluctuations were observed during procedurally demanding stages such as local anesthesia and rubber dam placement. The endodontist’s HR, as a physiological proxy for stress, was significantly influenced by the treatment difficulty level, stage, and the patient’s age. Conclusions: Using Apple Watch technology, our study revealed significant HR variations during different endodontic treatment stages, suggesting fluctuating physiological responses that may reflect occupational stress. Elevated HR was noted during patient examination and rubber dam placement, particularly in complex cases. These preliminary findings suggest that HR monitoring via wearable technology may serve as a useful, albeit indirect, indicator of occupational stress during endodontic procedures. Future studies with larger samples and additional validated stress biomarkers are needed to confirm these observations.