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The siege of Samarkand of July-October/ November 1496 was the first of a series of attempts made by Babur to seize the city. Although this first siege ended in failure Babur returned in the following year and successfully, if briefly, captured the city.
Babur was only one of three Timurid princes to take part in the siege. As their power declined the descendants of Tamerlane were increasingly prone to infighting, and the 1490s would be particularly disastrous for them. Babur inherited his kingdom of Fergana after the death of his father in 1494, and was almost immediately attacked by his uncle, Sultan Ahmad of Samarkand. Ahmad had died soon after abandoning the attack, and had been succeeded by his brother Muhmad, who died early in 1495 and was succeeded by his second son, Baisanghar.
Sultan Baisanghar had a short but eventful reign. During 1495 he was attacked by Sultan Mahmud of Tashkent, defeating him at the battle of Kan-bai, and then by Sultan Husain Mirza Baiqara of Khorasan. This second attack came to a halt outside Hisor, and after a siege that lasted for two and a half month the war was ended by a marriage between Sultan Husain Mirza Baiqara and one of Baisanghar's sisters.
Having seen off his external enemies Baisanghar fell foul of internal foes, some of the most powerful figures in Samarkand, who felt that he was favouring his childhood friends from Hisor. The Sultan was captured, and was on his way to the Guk Sarai, a building in the citadel used to crown, blind or strangle princes of the line of Timur, when he managed to escape. Baisanghar found a safe refuge where he was able to stay until a popular revolt put him back in power. His younger brother Sultan Ali, who had briefly held the throne, was sent to the Guk Sarai in turn, where he was to be blinded. In some way this went wrong, but Ali managed to disguise this, and a few days later took advantage of his sight to escape to Bokhara.
This triggered a civil war. Baisanghar led an army to Bokhara, but was defeated and forced to retreat to Samarkand. Ali Mirza followed, and laid siege to Samarkand. He was joined by his eldest brother, Sultan Mas'ud Mirza, who was motivated by the love of a daughter of one of the city's leaders. Once he had captured (or rescued) his love he lost interest in Samarkand and retired to Hisor!
Babur was the third participant in the siege. When news of the civil war reached him in Andijan (mid June-mid July 1496) he decided to attempt to seize Samarkand. The three relatives, all members of the Mirza family, besieged the city for three or four months, but with out any great success. Eventually, with winter coming near, and no sign of any shortages inside the city, the two remaining princes abandoned the siege, although only on the understanding that they would return in the following year and resume the attack.