This chapter’s central focus is how the Valley’s African Americans responded to the Emancipation Proclamation and Union general Robert H. Milroy’s enforcement of it in the northern Shenandoah Valley during the first six months of 1863. Additionally, this chapter focuses on the important roles filled by African Americans, such as Lee Jenkins, in General Milroy’s espionage operations. Furthermore, the chapter examines the fate of African Americans following General Milroy’s defeat at the Second Battle of Winchester. While untold numbers of African Americans escaped north into Pennsylvania, some of whom were seized by Confederates as they moved into the Keystone State, several hundred African Americans were captured by Confederate general Richard Ewell’s command near Stephenson’s Depot, north of Winchester, among them Lee Jenkins, who ultimately committed suicide to avoid enslavement. Through Jenkins’ story this chapter also explores the difficult decisions free blacks such as Jenkins confronted when seized by Confederates and impressed.