The Order's bailiffs of Narva were obligated to take charge of economic welfare of the town with the aim of defense maintenance. As one part of this task, the bailiffs were engaged in Livonian-Russian trade, including the control of the fulfillments of the Grand Master's prohibitions on the sale of sensitive goods, normally horses. At a time of escalation in Livonian-Russian relations the Masters did not allow the trade of "big or important" horses, i.e. those horses could be used for military purposes. At the same time, sources show that the Order's prohibitions were constantly violated not only by Russian and Livonian merchants, but also by representatives of the town authorities, in particular of Reval, therefore the bailiffs of Narva had quite large powers and had a right to put horses under arrest (as well as other goods, if they were excluded for export), in case the merchants did not have official documents allowing the export of such goods. However, even with such official documents, the bailiff could leave the horse in Livonia if he found it suitable for military purposes. Considering the fact that there were no other requirements except the ceiling price for an exported horse the horses bought in Reval often stayed at the border and the concluded deals cancelled. At the moment, the question of engagement of bailiffs of Narva in the system of Livonian-Russian trade relations is actually missed by researchers. This article outlines the role of bailiffs in the horse trade with Russia, and also traces the evolution dynamics of the Order's prohibitions over a period of the 15th century. Following on from the materials of the Tallinn city archive (fund 230, BB 52 I, BD 8) the author reasons that the significant role of bailiffs in the Livonian-Russian trade was dictated not only by the near-border position of the town, but also by the specific relations settled between the Livonian Order and Narva in the 15th century.