The operation was led by Military Governor Dmitry Romanovsky [ru] and aimed to capture several settlements on the Russo-Bukharan border including Khujand.

In practice, the city held extreme autonomy from both states, hosting both independent powers of governance, and a corresponding local identity and patriotism.

Romanovsky chose the Syr Darya route despite this concern, and in a letter to General Governor of Orenburg Nikolay Kryzhanovsky [ru] downplayed any negative consequences.

Structures and trees outside the fortress walls had been destroyed to reduce cover, and the main road to the city had been flooded by irrigation canals.

Romanovsky's aide-de-camp, who had remained in Tashkent, was forced to borrow 3,000 rubles from a wealthy local to fund the last transport to Khujand.

The columns were fired upon by Khujand forces with artillery and small arms, though they were still able to successfully identify a weak section in the north-eastern walls, and encircle the city.

[4][8] While Russian sources claim that during this time Kokandi military parties were approaching the city and agitating local villagers, historian Inomjon Mamadaliev has cast doubt on this due to the deep hostilities between Kokand and Khujand.

This drew defenders away from where the true attack was to be launched, and allowed Russian forces to fully cut off road access into the city.

A company in Mikhailov's column attempted to scale the walls with three siege ladders, though were repulsed when defenders began to shoot and throw stones at the attackers.

Many Khujandis attempted to flee the city on horseback, though a significant portion were killed or wounded by soldiers Romanovsky had ordered to guard the roads.

Russian forces began to bury the Khujandi dead, and provide rudimentary treatment for the wounded over several days.

While he had expected to impress the Russian government with the unapproved expedition similarly to Mikhail Chernyayev's capture of Tashkent, the Ministry of Foreign Affairs did not view the action positively.

[21] Romanovsky's expedition, particularly the captures of fort Nau and Khujand, intimidated the Kokand Khanate, who viewed the city as part of their state despite its independence.