Drawing on theoretical views of creative deviance, the present study hypothesized that employees with a tendency to break rules are more creative at their jobs (Hypothesis 1). Furthermore, we expected that this is particularly the case when employees face high problem-solving demands (i.e., they are expected to be creative) but at the same time they face high organizational constraints (e.g., they are not given the resources they need in order to be creative; Hypothesis 2). To test these expectations, we conducted a cross-sectional survey study (Study 1) and a daily diary survey study (Study 2) among employees from different occupational groups. Study 1 provided evidence that employee rule-breaking is related to other-rated employee creativity. Study 2 replicated this finding with a day-level measure of self-rated employee creativity. Furthermore, multilevel regression analyses revealed that the link is stronger when day-level problem-solving demands and organizational constraints are both high. Our findings contribute to the literature by providing empirical support to hardly examined propositions, namely, that non-compliant behaviors (i.e., rule-breaking) and obstacles (i.e., organizational constraints) may, in fact, boost creativity. Finally, suggestions for practice are made, recognizing the challenges posed to management in regulating employee rule-breaking.