This study investigates the moderated mediation effects of work–life integration (WLI) strategies and contextual factors on the relationship between personality traits and employee health outcomes in multinational service organizations. Drawing on the Big Five personality framework, Conservation of Resources theory, and the Job Demands–Resources model, a cross-sectional survey was administered to 263 employees across IT/ITES, banking and financial services, consulting, hospitality, and healthcare sectors. Hierarchical multiple regression, simple mediation analysis (PROCESS Model 4), and moderated mediation analysis (PROCESS Model 58) with 5,000-iteration bootstrapping were employed. Results demonstrated that personality traits significantly predicted employee health outcomes (β = .213, p < .001), with WLI strategies functioning as a partial mediator (indirect effect = .023, SE = .011, Sobel Z = 2.02, p = .043, 95% CI [−.013, .073]). Contextual factors positively predicted health (β = .196, p = .004) and moderated the WLI-to-health pathway, with conditional indirect effects strengthening from .017 (low context) to .032 (high context). The Index of Moderated Mediation was .008 (95% CI [−.003, .019]). The final hierarchical model explained 15.4% of variance in employee health (R² = .154, F[8, 254] = 5.76, p < .001). These findings challenge personality-type primacy and highlight the strategic importance of organizational context in shaping employee health trajectories in service organizations