Departing Baltimore on 3 November, Montezuma sailed as flagship of a squadron consisting of brig Norfolk, cutter Eagle, and schooner Retaliation for the West Indies.

Montezuma continued on her duty in the West Indies, convoying merchant ships to various Caribbean ports into 1799 and then on 7 March fell in with and captured French brig Les Amis, 16 guns, off Curaçao.

Montezuma was ordered home in mid-March and arrived Philadelphia on 12 May 1799 after convoying 57 merchant ships to various ports on the eastern seaboard.

This time she was bound for St. Kitts in the Leeward Islands, escorting U.S. shipping and then sailing to Jamaica to take on prize money, carrying it to Philadelphia, arriving Fort Mifflin on 31 July.

Re-equipped for merchant service, she sailed the Atlantic on a Baltimore-Liverpool run until disposed of some years before the beginning of the War of 1812.