Purpose - The aim of this paper was to investigate the role of perceived organizational support (POS) for employee risk-taking through its association with greater trust among supervisors and subordinates that the organization will take into account the individual's intent to be helpful in the case of failure (failure-related trust). Design/methodology/approach - Data were obtained from 346 employee-supervisor dyads from diverse organizations. Employees and supervisors described their PUS and failure-related trust. Supervisors also rated employee's risk-taking behaviors. Findings - Perceived organizational support (PUS) was positively related to failure-related trust among subordinates and supervisors which, in turn, was related to subordinates' risk taking. Additionally, supervisors' failure-related trust moderated the relationship between subordinates' PUS and failure-related trust, such that when supervisors strongly believed the organization was trustworthy in risk situations, employees' PUS had a stronger relationship with failure-related trust, which in turn, was related to risk-taking. Research limitations/implications - Understanding employee risk-taking has both theoretical, practical, and social implications. It advances our theoretical understanding of employee risk-taking and it shows the role played by managers in the promotion of subordinates' risk-taking behaviors. Originality/value - This is one of the first studies to examine the antecedents of employee risk-taking behaviors in the workplace. Additionally, it provides evidence for the key role played by supervisors in modeling subordinate's risk taking through social information processing. Another strength concerns the use of data from dyads (subordinates and supervisors), which helps us to overcome problems related to common method bias.