In late August 1862, Gen. Patrick R. Cleburne's division, the vanguard of Gen. Edmund Kirby Smith's infantry, moved out of Barbourville after Confederate Col. John Scott's victory over Col. Leonidas Metcalfe on Big Hill, with Barbourville's strong Union sentiment and scarce countryside supplies adding urgency to the advance. The division consisted of two brigades made up of eight infantry regiments and two four-gun artillery batteries, with Cleburne riding ahead of Gen. Benjamin Jefferson Hill's brigade of Tennessee and Arkansas infantry and a Tennessee brigade commanded by Col. Preston Smith following behind. When Hill's brigade reached Bobtown late on August 29, 1862, Scott met Cleburne and reported the Confederate front well picketed, but Cleburne, uneasy about relying on Scott's cavalry with an unknown enemy force ahead, shifted his infantry into a precautionary line of battle. He pushed Hill's line north of the Bobtown intersection and placed his infantry on high ground on both sides of the Old State Road (US 421), with pickets posted in front of the main line and before each position. The men slept on their arms, lying in line of battle with weapons at hand, unaware that Union Col. Leonidas Metcalfe's cavalry unit was moving toward them.