One of the most significant areas of guerrilla warfare during the American Civil War occurred along the Missouri-Kansas border. Many of these guerrilla forces had been active during the Bleeding Kansas period and continued their activities into the Civil War supporting the Confederacy. The guerrillas attacked Federal forces and disrupted their lines of communications, raided settlements in Kansas, and attempted to support Confederate conventional forces operating in the area. In 1864, Major General Sterling Price led a raid into Missouri in a final attempt to bring the state into the Confederacy. This thesis explores the nature of guerrilla warfare in the Missouri-Kansas border area and explains how Price and the guerrillas failed to employ the elements of Compound Warfare to bring Missouri into the Confederacy.