This study examines whether and when humble CEOs lead firms that behave more entrepreneurially. Guided by upper-echelons theory, we link CEO humility with corporate entrepreneurship, considering two specific discretionary sources in the firm’s task environment—market turbulence and market complexity—as moderators. We test our hypotheses using multi-source data from small Indian firms. We find that the association between CEO humility and corporate entrepreneurship is positive and significant, strengthening at higher levels of humility. Systematic post hoc analyses yield evidence for the moderating influence of market turbulence and complexity. Implications and directions for future research are discussed.