For some historians the conquest of Central Asia begins in 1865 with the fall of Tashkent to General M. G. Chernyaev. In fact this was the culmination of a series of steppe campaigns which had begun in the 1840s, but it did mark the point at which the Russian empire moved from the steppe to the settled zone of Southern Central Asia. Tashkent was Central Asia’s largest city and a major trading entrepôt, but it has long been argued that Chernyaev disobeyed orders when he captured the city. This chapter demonstrates that Chernyaev’s apparent disobedience was really a product of the ambiguity of his instructions, and above all of Russian ignorance of the geography of the region, which meant the War Ministry was convinced a ‘natural frontier’ would somehow present itself when it was needed. After Aulie-Ata, Chimkent and Turkestan had fallen to Russian forces, Chernyaev was instructed to separate Tashkent from the influence of Khoqand. While not quite the daring coup de main of legend, Chernyaev’s assault was risky, and resulted in two days of fighting in the streets before he reached an accommodation with the Tashkent ‘ulama. However, it was still unclear whether Tashkent would remain in Russian hands, or be turned into a city-state under Russian protection.