In April 1861, the American Civil War began with the Battle of Fort Sumter in nearby Charleston Harbor.
In the fall of 1861, Smalls was assigned to steer the CSS Planter, a lightly armed Confederate military transport under the command of Charleston's District Commander Brigadier General Roswell S. Ripley.
Planter's duties were to deliver dispatches, troops and supplies, to survey waterways, and to lay mines.
Smalls piloted the Planter throughout Charleston harbor and beyond, on area rivers and along the South Carolina, Georgia and Florida coasts.
From Charleston harbor, Smalls and the Planter's crew could see the line of federal blockade ships in the outer harbor, seven miles away.
Smalls appeared content and had the confidence of the Planter's crew and owners, and at some time in April 1862, Smalls began to plan an escape.
He discussed the matter with the other slaves in the crew except one, whom he did not trust.

On May 12, 1862, the Planter traveled ten miles southwest of Charleston to stop at Coles Island, a Confederate post on the Stono River that was being dismantled.
There the ship picked up four large guns to transport to a fort in Charleston harbor.
Back in Charleston, the crew loaded 200 lb (91 kg) of ammunition and 20 cord (72 m³) of firewood onto the Planter.
At some point, family members hid aboard another steamer docked at the North Atlantic wharf.

On the evening of May 12, the Planter was docked as usual at the wharf below General Ripley's headquarters.
Its three white officers disembarked to spend the night ashore, leaving Smalls and the crew on board, "as was their custom."
  (Afterward, the three Confederate officers were court-martialed and two convicted, but the verdicts were later overturned.)
At about 3 a.m. May 13, Smalls and seven of the eight slave crewmen made their previously planned escape to the Union blockade ships.
Smalls put on the captain's uniform and wore a straw hat similar to the captain's.
He sailed the Planter past what was then called Southern Wharf and stopped at another wharf to pick up his wife and children and the families of other crewmen.

Smalls guided the ship past the five Confederate harbor forts without incident, as he gave the correct signals at checkpoints.
The Planter had been commanded by a Captain Charles C. J. Relyea and Smalls copied Relyea's manners and straw hat on deck to fool Confederate onlookers from shore and the forts.
The Planter sailed past Fort Sumter at about 4:30 a.m. The alarm was only raised after the ship was beyond gun range.
Smalls headed straight for the Union Navy fleet, replacing the rebel flags with a white bed sheet which was brought by his wife.
The Planter had been seen by the USS Onward, which was about to fire until a crewman spotted the white flag.
In the dark, the sheet was difficult to see, but the sunrise arrived which allowed viewing.

Witness account:
Just as No.
3 port gun was being elevated, someone cried out, "I see something that looks like a white flag"; and true enough there was something flying on the steamer that would have been white by application of soap and water.
As she neared us, we looked in vain for the face of a white man.
When they discovered that we would not fire on them, there was a rush of contrabands out on her deck, some dancing, some singing, whistling, jumping; and others stood looking towards Fort Sumter, and muttering all sorts of maledictions against it, and "de heart of de Souf," generally.
As the steamer came near, and under the stern of the Onward, one of the Colored men stepped forward, and taking off his hat, shouted, "Good morning, sir!
I've brought you some of the old United States guns, sir!"
That man was Robert Smalls.

The Onward's captain, John Frederick Nickels, boarded the Planter, and Smalls asked for a United States flag to display.
He surrendered the Planter and its cargo to the United States Navy.
Smalls' escape plan had succeeded.

The Planter and description of Smalls' actions were forwarded by Lt.
Nickels to his commander, Capt.
E.G. Parrott.
In addition to its own light guns, Planter c
In April 1861, the American Civil War began with the Battle of Fort Sumter in nearby Charleston Harbor. In the fall of 1861, Smalls was assigned to steer the CSS Planter, a lightly armed Confederate military transport under the command of Charleston's District Commander Brigadier General Roswell S. Ripley. Planter's duties were to deliver dispatches, troops and supplies, to survey waterways, and to lay mines. Smalls piloted the Planter throughout Charleston harbor and beyond, on area rivers and along the South Carolina, Georgia and Florida coasts. From Charleston harbor, Smalls and the Planter's crew could see the line of federal blockade ships in the outer harbor, seven miles away. Smalls appeared content and had the confidence of the Planter's crew and owners, and at some time in April 1862, Smalls began to plan an escape. He discussed the matter with the other slaves in the crew except one, whom he did not trust.
On May 12, 1862, the Planter traveled ten miles southwest of Charleston to stop at Coles Island, a Confederate post on the Stono River that was being dismantled. There the ship picked up four large guns to transport to a fort in Charleston harbor. Back in Charleston, the crew loaded 200 lb (91 kg) of ammunition and 20 cord (72 m³) of firewood onto the Planter. At some point, family members hid aboard another steamer docked at the North Atlantic wharf.
On the evening of May 12, the Planter was docked as usual at the wharf below General Ripley's headquarters. Its three white officers disembarked to spend the night ashore, leaving Smalls and the crew on board, "as was their custom."   (Afterward, the three Confederate officers were court-martialed and two convicted, but the verdicts were later overturned.) At about 3 a.m. May 13, Smalls and seven of the eight slave crewmen made their previously planned escape to the Union blockade ships. Smalls put on the captain's uniform and wore a straw hat similar to the captain's. He sailed the Planter past what was then called Southern Wharf and stopped at another wharf to pick up his wife and children and the families of other crewmen.
Smalls guided the ship past the five Confederate harbor forts without incident, as he gave the correct signals at checkpoints. The Planter had been commanded by a Captain Charles C. J. Relyea and Smalls copied Relyea's manners and straw hat on deck to fool Confederate onlookers from shore and the forts. The Planter sailed past Fort Sumter at about 4:30 a.m. The alarm was only raised after the ship was beyond gun range. Smalls headed straight for the Union Navy fleet, replacing the rebel flags with a white bed sheet which was brought by his wife. The Planter had been seen by the USS Onward, which was about to fire until a crewman spotted the white flag. In the dark, the sheet was difficult to see, but the sunrise arrived which allowed viewing.
Witness account:
Just as No. 3 port gun was being elevated, someone cried out, "I see something that looks like a white flag"; and true enough there was something flying on the steamer that would have been white by application of soap and water. As she neared us, we looked in vain for the face of a white man. When they discovered that we would not fire on them, there was a rush of contrabands out on her deck, some dancing, some singing, whistling, jumping; and others stood looking towards Fort Sumter, and muttering all sorts of maledictions against it, and "de heart of de Souf," generally. As the steamer came near, and under the stern of the Onward, one of the Colored men stepped forward, and taking off his hat, shouted, "Good morning, sir! I've brought you some of the old United States guns, sir!" That man was Robert Smalls.
The Onward's captain, John Frederick Nickels, boarded the Planter, and Smalls asked for a United States flag to display. He surrendered the Planter and its cargo to the United States Navy. Smalls' escape plan had succeeded.
The Planter and description of Smalls' actions were forwarded by Lt. Nickels to his commander, Capt. E.G. Parrott. In addition to its own light guns, Planter c
Robert Smalls