This study examines the moderating role of personality traits in the relationships between job stress, psychological well-being, and turnover intentions among 245 secondary school teachers (80 males, 165 females) in Karachi, Pakistan. Data was collected using purposive sampling from private and government schools. The research evaluates how personality domains (extraversion, agreeableness, conscientiousness, emotional stability, openness) and job stress influence psychological well-being and turnover intentions, while considering demographic factors like gender, institution type, job nature, marital status, and teaching experience. Findings reveal workplace stress negatively predicted psychological well-being (β = -.976). Personality traits significantly influenced the job stress-well-being relationship, with higher extraversion, agreeableness, conscientiousness, and openness weakening job stress's negative impact, aligning with transactional stress-coping models. Unexpectedly, emotional stability strengthened the positive job stress-turnover intention link. Significant negative correlations existed between well-being and job stress (r = -.978), and well-being and turnover intention (r = -.971). Personality traits positively predicted turnover intentions. The moderating effects were statistically significant for extraversion (B = .021), agreeableness (B = .0184), conscientiousness (B = .022), emotional stability (B = .021), and openness (B = .0238). The study highlights implementing stress management and fostering positive personality traits to enhance educator well-being and retention. By identifying protective and risk factors, tailored interventions and policies can improve teachers' work-life quality and promote a conducive learning environment.