Before the Civil War, 75 enslaved people toiled at Rippavilla, many working the fields there. After the January 1, 1863, Emancipation Proclamation, although Tennessee was exempt because it was under Federal control, many enslaved people in the region sought freedom when news of the decree reached them, and some African American men volunteered for the US Army. Joshua and Phillip, enslaved at Rippavilla since birth, fled in the late summer of 1863 and enlisted in the 12th United States Colored Troops. About a year later, Phillip was killed by a civilian while foraging for food. On December 16, 1864, Joshua's 12th USCT, together with the 13th and 100th USCT in Col. Charles R. Thompson's Second Colored Brigade, attacked Confederates holding Overton Hill south of Nashville. Joshua survived the war and was discharged in June 1865. Another man enslaved at Rippavilla, Jerry, fled, enlisted in the 111th USCT, and was captured at Sulphur Creek Trestle in September 1864. Because the Confederate government did not exchange Black prisoners of war, men like Jerry were returned to slavery, while other captured soldiers from the 111th USCT were sent to work on fortifications at Mobile, Ala., a fate Jerry likely also shared. He survived the war and was discharged from the Army in mid-1865.