The article presents a comparative analysis of paradiplomatic activity of the subjects of the Russian Federation and Canadian provinces. Special attention is given to political and legal aspects of paradiplomacy. It shows similarities and differences between the Russian and Canadian models of federalism as well as the legal status of subjects' external relations, their forms and methods. It is emphasized that the evolution of contemporary Canadian Federalism follows the formula of de jure symmetry with de facto asymmetry. On the one hand, such combination helps to avoid conflicts between provinces and gives them opportunity to achieve their specific goals and interests while remaining respectful members of the Federation. The author shows the specificity of Quebec Identity Paradiplomacy and the role of Gérin-Lajoie doctrine in its development. The article stresses those aspects of Canadian provinces' paradiplomatic experience that could be applicable for subjects of the Russian Federation, which are currently taking an increasingly active part in the implementation of Russia's foreign policy.