This article focuses on two main issues: the ability of informal cross-border entrepreneurs to avoid restrictions imposed by a government, and governmental capacity to make these restrictions work efficiently in the long term. Two kinds of informal trade activities between Russia and Japan—import of used cars and trafficking of marine bioresources—are taken as case studies. I argue that in both cases informal cross-border traders have tried to exploit cross-border differences to their benefit, balancing between legal, low-punishable, and heavily punishable practices. Both kinds of informal trade proved to be highly resistant to suppressive government policies and highly capable of exploiting legal and law enforcement loopholes. Still, suppressive government policies proved to be at least partially successful in the long term.