Hale was originally commissioned in the 12th Infantry Regiment and was stationed at Fort Niagara. He and his regiment went to Fort Bennett in 1886, and he participated in the Sioux Wars while there. He was recommended for the Medal of Honor, though he ultimately did not receive it. Hale was in charge of Sioux prisoners in 1891, and he served as an aide to Wesley Merritt from 1893 to 1899, meaning he served in the Philippines during the Spanish–American War. He also served as an aide to Arthur MacArthur Jr. Hale commanded the 44th Volunteer infantry during the Philippine–American War, and he commanded Bilibid Prison in 1902. He also served as the acting commander of the 20th Infantry Regiment during the Battle of Luzon.