While emerging studies pay much attention to the supervisory support–employee performance relationship, the supportive supervisor consequences on employees’ attitudes and behaviors have attracted little attention in this relationship. In spite of the growing concern about employees’ helping behaviors as a tool that directly benefit coworkers to be work-role focused and improve performance, supportive supervisor behavior that represents the psychological, physical, cognitive, and esteem assistance has also been deemed to be a catalyst of employees’ helping behaviors. Also, it is worth noting that employees exhibit helping behaviors when they are highly engaged in work role focus, activation, and positive affect. However, little has been espoused on how supportive behaviors could enhance employees’ loyalty to spark helping behaviors. Owing to this narrative, this study draws on social exchange theory and reciprocity norm to examine the mediating role of employee engagement in the effects of supportive supervisor behavior on hotel employees’ helping behaviors. Also, this study examined the boundary role of perceived organizational obstruction based on perceived organizational support as proposed by organizational support theory. Using a time lag of six months, a two-wave data were gathered from 461 full‒time frontline employees working in 3–5 star hotels in Ghana. Hierarchical regression was used to analyze the hypothesized relationships. The results demonstrated that supportive supervisor behavior positively related to employees’ helping behaviors. Besides, intellectual, social, and affective engagement partly mediated the relationship between supportive manager behavior and employees’ helping behavior. Moreover, perceived organizational obstruction moderated the relationship between intellectual engagement and employees’ helping behavior. However, failed to moderate social and affective engagement relationships with employees’ helping behaviors.