Assigned to the North Atlantic Squadron, the new cruiser operated along the eastern seaboard and in the Caribbean. During the Spanish–American War, she cruised near Cuba and Haiti in April 1898 and in May joined the blockade of Havana. She took two prizes, Lorenzo and Frasquito, 5 May, and shelled the Spanish forts a week later.[4] On 13 June a 280mm Kruppgun at the Santa Clara Battery fired on Montgomery, at a range of 9,000 meters, apparently without effect.
In April 1899 Montgomery transferred to the South Atlantic Squadron and operated along the Atlantic coast of South America . In July 1900 she was import Urgaguy with CDR JohnMerrill as her Commanding Officer. (US Census 2 July 1900, lists crew members.) She returning to the United States and decommissioning at New York City 15 September 1900. Recommissioned 15 May 1902, she was assigned to the Caribbean Division, North Atlantic Squadron, and operated in the West Indies until decommissioning at Philadelphia, Pennsylvania 15 September 1904.[4]
Montgomery recommissioned 2 January 1908 and operated in the 5th Naval District as a torpedo experimental ship. From 1914 to 1918 she served with the Maryland Naval Militia. Renamed Anniston 14 March 1918, she was assigned to Division 2, American Patrol Detachment, for patrol and escort duty along the Atlantic coast and in the Caribbean.[4]