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 all the other slaves in the crew except one, whom he did not trust.