Despite the growing practice and improving efficiency of toll road use in Russia, legislative regulation in this area lags behind its actual development. Uncertainty in the legal qualification of relations concerning the provision of the right of passage and related services, the absence of standard contractual forms, and the lack of established practice in using digital platforms create barriers to proper legal and contractual regulation of relations between operators and users. Contractual regulation of relations related to the use of toll roads is characterized by a combination of private-law and public-law principles. Digital platforms create new opportunities for improving contractual regulation but require specific legal mechanisms for the protection of personal data and cybersecurity.