On 18 November 1495, Bielsk Podlaski received a city charter based on Magdeburg rights from the Grand Duke of Lithuania, Alexander Jagiellon.
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On 18 January 1493, Brańsk received a city charter based on Magdeburg rights from the Grand Duke of Lithuania, Alexander Jagiellon.
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A series of privileges by the Grand Dukes (by Sigismund Kęstutaitis in 1434, Casimir IV Jagiellon in 1447, Alexander Jagiellon in 1492, Sigismund I the Old in 1507) released veldamai from their taxes to the state.
In 1500 Plettenberg made an alliance with Grand Duke of Lithuania, Alexander Jagiellon (the Treaty of Wenden), who was in war with Russia since 1499.