This study investigates the impact of occupational stress on employee well-being and employee engagement in selected private insurance companies in Karnataka. Using a structured quantitative approach, the research explores how varying levels of job-related stress influence the psychological and emotional states of employees, ultimately affecting their level of engagement at work. Tools such as descriptive statistics, correlation analysis, and multiple regression were used to analyze primary data collected from 346 respondents. The findings reveal a significant inverse relationship between occupational stress and both employee well-being and engagement. This research offers valuable insights for HR managers, mental health professionals, and policymakers aiming to foster healthier, more resilient insurance workforces.