Confederate authorities were quite upset over Robert Smalls' escape with the Planter. The steamer was assigned to the Confederate headquarters in Charleston under the personal direction of General Roswell S. Ripley, commander of the Second Military District of South Carolina.
Ripley used Planter to carry orders, supplies, and ordnance to the various military posts throughout Charleston Harbor and the adjacent sea islands.
The steamer's crew consisted of three white officers (C. J. Relyea, captain; Samuel H. Smith, pilot; and Zerich Pitcher, engineer) and eight slaves.
Planter, most embarrassingly for the Confederates, was stationed at a wharf directly in front of Ripley's headquarters in the city of Charleston. Robert Smalls had literally stolen Planter right from under the Confederates' noses.
Robert and the Planter's enslaved crew had been plotting their escape for several weeks. They decided that the best way to gain their freedom was to sail their vessel out to the Federal Navy's blockading ships.
An opportunity arose on the evening of 12 May when all three of Planter's white officers, against direct orders from Confederate authorities, decided to spend the night on shore. That afternoon the steamer received a cargo of four heavy cannons scheduled for delivery to forts in Charleston Harbor the next day.
Before leaving the vessel, Captain Relyea ordered Robert Smalls (the ranking member of the slave crew) to have Planter ready to sail at first light.