Contemporary scholars in vocational, applied, and organizational psychology have emphasized that working must be understood as a relational act with important implications for worker well-being. Drawing upon emergent research extending the constructs of adult attachment security and authenticity to the workplace, this study tested a positive psychological model linking adult attachment orientations, and both experienced and expressed features of work authenticity, to the prediction of well-being within a sample of business managers. Findings indicated that, controlling for their gender and length of managerial experience, managers’ levels of adult attachment security and work authenticity accounted for significant and incremental variance in their reported levels of work stress and job satisfaction. In general, managers with high levels of adult attachment security and work authenticity reported lower work stress and higher job satisfaction. Implications of these findings for the counseling of distressed managers are briefly discussed.