Organized by Comm. John Taylor Wood in early February 1864, the expedition against the USS Underwriter, in the Neuse River near New Bern, North Carolina, was part of a larger Confederate effort to recapture the city from the occupying Federal forces. Wood's force consisted of 220 enlisted sailors and Marines, as well as thirty-three officers. These forces converged on Kinston, North Carolina from around the Confederacy, including Wilmington Station, Charleston Station, the Savannah Squadron, and the James River Squadron.
Divided into two detachments comprised of twelve boats and two launches, the expedition descended the Neuse River and rendezvoused at Bachelor's Creek, just upstream from New Bern. Wood, his executive officer, Lt. Benjamin Loyall, and a small crew of experienced men reconnoitered the area after nightfall on February 1 and selected the USS Underwriter as their target. Anchored in the river alone, adjacent to the Federal batteries of Fort Stephenson, the Underwriter was a side wheel steamship that measured 186 feet long, thirty-five feet wide, and weighed 325 tons. She was armed with two 8-inch guns, a 30-pounder rifle, and a 12-pounder boat howitzer, and she was commanded by Acting Master Jacob Westervelt.
At 2:30 a.m. on February 2, the attack commenced with Wood's detachment striking forward of the Underwriter's wheel. Loyall's detachment reached the vessel first and struck aft of the wheel. Confederate Marines stationed in each boat functioned as sharpshooters, while the two launches were kept in a reserve role. Sailors on the Underwriter spotted the raiders and opened fire. However, after just a few minutes of fierce hand-to-hand combat, the Confederates gained control of the ship.
Much to their dismay, Confederate engineers found no steam in the Underwriter's boilers and estimated that it would be as much as an hour before the ship could be moved. Wood did not have time to wait, as the batteries of Fort Stephenson opened fire on the Confederate party. Realizing the vessel would have to be scuttled, Wood gave the order to set fire to the ship. The Confederates boarded their boats and rowed to safety upriver, watching the Underwriter explode as the fire reached her powder magazine. Upon their return to Kinston, most of the Confederate sailors were sent back to their previous duty stations, but a few of the officers were retained to take new positions on board the Confederate ironclad, CSS Neuse; Loyall was given command of the gunboat. While the overall attack on New Bern failed, the Confederate Navy demonstrated that the occupying forces in eastern North Carolina were still vulnerable in the spring of 1864.