This study aims to contribute to the research on bootlegging by investigating (i) whether employees’ risk propensity explains why some secretly organise innovation, whereas others do not, and (ii) how direct management support for compliant innovative behaviour affects this relationship. Answers to these questions are relevant because managers experience bootlegging in their organisations but do neither know from which employees they can expect creative deviance nor how to regulate it. Drawing on risk behaviour theory, risk propensity is supposed to foster bootlegging behaviour, and different forms of management support moderate this relationship by changing the salience of opportunities and the threats inherent in “going underground”. The empirical results provide ample support for the direct impact of risk propensity. This effect becomes weaker when managers provide more support in the form of resources and feedback, whereas encouragement to innovate strengthens the relationship.