The first Osceola, a wooden, side-wheel, double-ended gunboat was launched 29 May 1863 by Curtis and Tilden, Boston; delivered to the Navy at the Boston Navy Yard 9 January 1864; and commissioned there 10 February 1864, Comdr. J. M. B. Cletz in command.

Osceola departed Boston 22 April, towing monitor Canonicus, and reached Hampton Roads 3 May. The next night, the double-ender got underway up the James River in a joint Army-Navy expedition and helped clear a safe path through the Confederate mine field for sister ships and Army transports. The troops landed at Bermuda Hundred, Va. in an operation helping Grant to tighten his squeeze on Richmond.

In ensuing months Osceola continued operations on the James River supporting Grant's relentless offensive. She and Miami drove off Southern batteries which were firing on Union transports near Harrison's Landing, Va. This and similar Naval efforts to protect Grant's lines of supply and communications contributed greatly to the success of the campaign against the Confederate capital.

Late in December, Osceola steamed down the coast for the joint attack on Ft. Fisher which protected Wilmington. The Union troops withdrew from their beachheads on Christmas Day, but the Naval commander, Rear Adm. Porter was not to be denied. He returned to the Cape Fear River 13 January and, after 3 days fighting, Ft. Fisher fell. Osceola decommissioned at Boston Navy Yard 13 May 1865 and was sold at auction 1 October 1867.