The ruin of the town was accelerated by the Rising of 1798 . Prosperous was one of the first places where the United Irishmen rose. In the early morning of 24 May 1798, a large group of rebels attacked the crown forces in the town. One of the buildings holding over 50 men, including the leader, Captain Swayne, was burned. Oral tradition relates that the rebels were led by Andrew Farrell and John Esmonde and assisted by Ruth Hackett in the burning of the barracks. She is featured on the 1798 monument in the town square. The rebels held Prosperous until the crown forces recaptured it on the 19th of June. The troops were under the command of Colonel Stewart who boasted of destroying "this receptacle of rebellion". He said that the soldiers found drums with the inscription "Prosperous Strength Exists in Unity and Liberty".