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Digital technologies made it possible to reduce the degree of information asymmetry, thereby digitisation is proposed to overcome an agency problem or free-riding. By enhancing a monitoring performance, the digital technologies also increase the probability of crime uncovering, which according to Becker’s crime and punishment theory lead to greater deterrence. However automated systems could themselves act as a source of moral hazard, resulting from a lack of user awareness about the underlying principles of the system. In this research we propose an integrative theoretical framework, combining marginal deterrence approach and agent problem. Using the example of the Russian Federal Tax Service, we show how the exploitation of an automated tax control system in a presence of moral hazard give rise to enforcement errors both Type I and Type II, which limit the deterrent function of enforcement, making illegal behaviour more attractive.