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Insurgent organizations have become major players in criminal enterprises around the world. However, research examining why some participate in crime while others do not remains underdeveloped. Analyzing newly collected annual data on 140 insurgent groups from 1998 to 2012, we examine the conditions driving insurgents’ participation in drug crimes, extortion, smuggling, kidnapping for ransom, and robbery. We find that control of territory positively affects involvement in all types of crime. However, we also find notable differences in the conditions driving participation in episodic crimes versus crimes that require institutional investments. Institutional crimes are, with the exception of smuggling, more likely to occur as insurgent groups age, whereas efforts to cultivate legitimacy—as indicated by the ongoing provision of social services—substantially reduces the probability of involvement in episodic crimes. We …