Abstract: The subject of this article is the problems associated with ensuring transportation safety n the Moscovian State of the XVI-XVII centuries. The author examines the conditions and causal links that influenced the choice of certain measures for ensuring transportation safety. Analysis is conducted on the new to the Moscovian State practice of granting administrative monopoly on ensuring transportation safety to meet the interests of the representatives of certain foreign countries and corporations. The factors substantiating the implementation of administrative monopoly are explained. The algorithm for resolving the cases associated with infringement on the security of English transports in the Moscovian State is described. The scientific novelty of this research consists in determination of noncompliance of the goals of ensuring transportation safety that were claimed in the normative documents (Charters of the Russian tsars of the XVI-XVII centuries) with the actual capabilities and practice for its provision. The conclusion is made that the guarantees of the English sea transportation indicated in the charters of Moscovian tsars should be viewed merely as the declaration of good intentions, rather than factual help. The comparative legal analysis of archival documents allows establishing the fact the English kings interpreted charters of the Moscovian tsars on their own behalf, granting the English nationals the rights and privileges in the area of transportation safety.