After the arrival of the expedition party in Bermuda, Wilkinson took command of a privately owned blockade runner, Whisper, which had come over from England in the early part of 1864. Tabb accompanied him back to the Confederacy, where they parted ways.

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In May 1864, Tabb ran the blockade for the 20th time from Wilmington to Bermuda. It was a particularly difficult crossing, in rough weather, on a poor steamer burning bad coal. Tabb remembered that it was a Sunday when they landed because the bell of the English church was ringing, and he got ashore just in time to attend the evening service.

Tabb had come bearing government dispatches, and was under orders to return on Siren, a small British steamer used by the governor of Bermuda as a yacht, which had been purchased by the Confederate government. Siren, which was commanded by a British captain, was in poor condition, and the captain had trouble getting a crew. She was very noisy, "roaring like a buzz saw," Tabb said, and someone remarked that the blockading fleet would hear her coming before they saw her. On the third day at sea there was a report, which proved false, that she had sprung a leak and was going to sink. But something had definitely gone wrong with the engine, and the ship was almost dead in the water. On the morning of June 5, 1864, off Beaufort, N.C., Siren was approached by the Federal steamer Keystone State, which fired two shots over her bow. The British flag was lowered, and Siren was towed into port by Keystone State as a prize of war.

Tabb, the British captain and others were sent to Point Lookout, the infamous Federal prison camp located on a low, sandy peninsula in southern Maryland where the Potomac River meets the Chesapeake Bay. The prison was about 20 acres in size, surrounded by a palisade and heavily guarded. The prisoners were housed in tents, although there was an extensive hospital for the ill–of whom there were many. There, Tabb spent the most miserable seven months of his life. He corresponded with the British representative in Washington and secured his cooperation in getting the captain and his associates released from Point Lookout. They were prepared to declare him English also, to secure his release, but Tabb would have none of this. When the Englishmen reached New York, they sent, by prearrangement, a box of supplies to Tabb, which included a $5 gold piece concealed in a sausage. Being sick in the hospital at the time, Tabb somehow forgot the money and gave the supplies away. The honest recipient of the sausage later returned the $5 gold piece to him.

The only bright spot in Tabb's imprisonment was his meeting with Sidney Lanier, a young Confederate signal officer who also had been captured aboard a blockade runner. Lanier, who would become one of the South's best-known postwar literary figures, was an accomplished flutist. While in the hospital, Tabb heard the sound of a flute, which Lanier had smuggled into prison concealed up his sleeve, and vowed that he must find the player when he was able. The two kindred spirits became inseparable until their release from prison. They were together as much as possible, frequently being joined by a Polish physician with a fine voice who loved to sing operatic arias. Often, when singing a love song, the good doctor would work himself up to an emotional peak, much to the amusement of the young Americans.

In February 1865, Tabb was finally exchanged and went home to The Forest in Amelia County, where he remained until April, recuperating from his prison ordeal. He then joined his brothers' regiment, the 59th Virginia Infantry stationed near Richmond, at about the time that the capital city was evacuated. The 59th, commanded by his older brother, Colonel William Barksdale Tabb, was part of Brig. Gen. Henry A. Wise's brigade. As the Army of Northern Virginia withdrew southwestward, closely pursued by Federal forces, it passed through Tabb's home county. A portion of the army was surrounded at the Battle of Sayler's Creek on April 6, 1865. Most of the encircled Confederates were obliged to surrender, but Wise's brigade fought its way out of the trap and became part of Maj. Gen. John B. Gordon's command on the march to High Bridge, Farmville, and Appomattox Court House. There, on April 9, 1865, just past his 20th birthday, Private John B. Tabb was paroled along with his brothers and the remaining members of the 59th Virginia Infantry.

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