Researchers have suggested that both ambiguity and values play important roles in shaping employees’ proactive behaviors, but have not theoretically or empirically integrated these factors. Drawing on theories of situational strength and values, we propose that ambiguity constitutes a weak situation that strengthens the relationship between the content of employees’ values and their proactivity. A field study of 204 employees and their direct supervisors in a water treatment plant provided support for this contingency perspective. Ambiguity moderated the relationship between employees’ security and prosocial values and supervisor ratings of proactivity. Under high ambiguity, security values predicted lower proactivity, whereas prosocial values predicted higher proactivity. Under low ambiguity, values were not associated with proactivity. We replicated these findings in a laboratory experiment with 232 participants in which we measured proactivity objectively as initiative taken to correct errors: Participants with strong security values were less proactive, and participants with strong prosocial values were more proactive, but only when performance expectations were ambiguous. We discuss theoretical implications for research on proactivity, values, and ambiguity and uncertainty.