Annotation

This article examines the institutional evolution of special tax regimes-the Professional Income Tax (PIT) and the Automated Simplified Tax System (ASTS)-in the context of government policy on digitalization and legalization of the economy. Based on an analysis of regulatory documents, data from the Federal Tax Service of the Russian Federation, and academic research, the contradictory nature of these instruments is revealed: a combination of stimulating fiscal "contracts" and restrictive restrictions. The authors substantiate the concept of the PIT and ASTS as a single evolutionary fiscal experiment, the key failure of which is its temporary nature, which generates legal uncertainty and hinders long-term investment decisions. It is argued that a sustainable effect requires systemic harmonization and integration of their key digital principles into the permanent legal framework of the Tax Code of the Russian Federation, which will ensure the transition from an experimental to a stable regulatory model.