When in September 1999, the Russian army entered Chechnya after the Chechen incursion in Dagestan and the Russian apartment bombings, Said was able to return to Northern Chechnya. He was appointed deputy head of the Nadterechny district administration. In December 1999 he joined the Russian army. With some of his fellow anti-Maskhadov rebels, he formed a special-purpose company of the 42nd motorized rifle division of the Russian army (the first Chechen unit on the Russian side in the Second Chechen War) and entered Grozny. Kakiyev claimed his unit was the first to hoist the Russian flag in Grozny. During the Battle of Komsomolskoye, forces commanded by Kakiyev managed to surround forces commanded by Ruslan Gelayev.