Drawing from the Conservation of Resources Theory, this paper aims to study the impact of an emerging destructive leadership style termed punitive supervision on employee well-being by examining the mediation role of work alienation. This paper further explains conditional indirect effects by introducing employee willpower and waypower as employees’ coping mechanisms to deal with the damaging effects of punitive supervision. Three-wave data (N = 265) obtained from frontline employees of the hotel industry across Pakistan were used to test the hypothesized moderated mediation model. Findings reveal that punitive supervision impacts work alienation which results in diminished employee well-being. The mediated and moderated relationships were established. The indirect conditional relationships were supported, providing the insight that employee willpower and waypower reduce the negative effects of punitive supervision on employee well-being via work alienation. This study offers managers valued insights on formulating efficient strategies to enhance employee well-being and eliminate adverse consequences of punitive supervision on employees.