Lithuania-Moscow war begins

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In 1499, after years of brewing, conflict between Lithuania and Moscow broke out into a war. In previous clashes, Moscow had beaten Lithuania and captured some of its domains. The current war broke out because of the marriage of Lithuania's grand prince Aleksandras and Moscow's Ivan III daughter. Aleksandras tried to force his wife into Catholicism, Ivan found this unacceptable. Tensions grew and soon full scale war broke out.

The war created controversial feelings in Livonia. On the one hand, the Livonians could breathe easy, because even after the war with Sweden had ended, Russia was unable to send its full forces against them. Yet, from early on the fate seemed to favour Moscow and it became possible that Ivan III will conquer Eastern-Lithuania, with which also the town of Polotsk and the upper reaches of Väina River will fall to the Russians. This would have meant that Livonia will share also the southern border with Russia. This was something that Plettenberg wanted to avoid at all costs, and thus Lithuanians and Livonians opened negotiations. At last, Livonia got its chance to fight Moscow, previous anti-Moscow alliance negotiations with Denmark and Sweden had failed.

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