The turn of the nineteenth century saw an increasing encroachment of Russian explorations into and around isolationist Japan, culminating with the capture and imprisonment of Russian naval captain Vasily Golovnin in 1811. These Russian attempts to “open” Japan were a threat to the established contact between Japan and Europe through the Dutch base in Dejima at Nagasaki, which gave the Dutch a monopoly on relations and the transfer of knowledge between Japan and Europe. However, Russia’s imperial designs in the North Pacific and the Napoleonic wars, which reduced Dutch power, threatened this monopoly, offering new perspectives on Japan and throwing political relations with the Japanese Shogunate (Bakufu) into turmoil. This paper compares Dutch and Russian approaches to contact with Japan at the turn of the nineteenth century and examines how actions such as Golovnin’s imprisonment foreshadowed an end for Japanese isolationism and the Dutch monopoly on contact with the Shogunate.