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The Second Chechen War, in a later phase better known as the War in the North Caucasus was launched by the Russian Federation starting August 26, 1999, in response to the Invasion of Dagestan by the IIPB.

On 1 October, Russian troops entered Chechnya. The campaign ended the de-facto independence of Chechen Republic of Ichkeria and restored Russian federal control over the territory. Although it is regarded by many as an internal conflict within the Russian Federation, the war attracted a large number of foreign fighters.

During the initial campaign, Russian military and pro-Russian Chechen paramilitary forces faced Chechen separatists in open combat, and seized the Chechen capital Grozny after a winter siege that lasted from late 1999 to the following February 2000. Russia established direct rule of Chechnya in May 2000 and after the full-scale offensive, Chechen guerrilla resistance throughout the North Caucasus region continued to inflict heavy Russian casualties and challenge Russian political control over Chechnya for several more years. Some Chechen rebels also carried out terrorist attacks against civilians in Russia. These terrorist attacks, as well as widespread human rights violations by Russian and rebel forces, drew international condemnation.

As of 2009, Russia has severely disabled the Chechen rebel movement and large-scale fighting has ceased. Russian army and interior ministry troops no longer occupy the streets. The once leveled city of Grozny has recently undergone massive reconstruction efforts and much of the city and surrounding areas have been rebuilt at a quick pace. However sporadic violence still exists throughout the North Caucasus; Occasional bombings and ambushes targeting federal troops and forces of the regional governments in the area still occur.

On 16 April 2009, the counter-terrorism operation in Chechnya was officially ended. As the main bulk of the army was withdrawn, the burden of dealing with the ongoing low-level insurgency mainly fell on the shoulders of the local police force. Three months later, the exiled leader of the separatist government, Akhmed Zakayev, called for a halt to armed resistance against the Chechen police force starting on August 1, and said he hoped that "starting with this day Chechens will never shoot at each other".

The exact death toll from this conflict is unknown. Unofficial estimates range from 25,000 to 50,000 dead or missing, mostly civilians in Chechnya. Russian casualties are over 5,200 (official Russian casualty figures) and are about 11,000 according to the Committee of Soldiers' Mothers.

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