Hiring the tugboats for the mission proved to be the most difficult task of all for Fox. Because obvious danger surrounded the endeavor, Northern shipowners were reluctant to lend their tugs to the cause. Only the payment of the most exorbitant rates, Fox complained, finally secured the services of three tugs–Yankee, Uncle Ben and Thomas Freeborn.

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Other problems also plagued Fox's preparations. The quality of the troops provided by the U.S. Army for the mission left something to be desired. Fox later complained that the soldiers were totally unfit to be thrown into a fort likely to be attacked by the rebels.

Fortunately for Fox, obtaining supplies to provision Fort Sumter was a simpler task. He found a staunch supporter in Major Amos B. Eaton of the Commissary Department, who thanked God that an attempt was made to relieve Major Anderson's command and immediately provisioned for all contingencies.

Finally, when all preparations for Fox's mission were complete, the various vessels sailed for Charleston. Each made its way south separately. On April 6 the frigate Powhatan, under the command of Captain Samuel Mercer, prepared to sail from New York. Other vessels, including the revenue cutter Harriet Lane and tugs Uncle Ben and Yankee, soon made their way south. The sloop of war Pawnee, under the command of Commander Stephen C. Rowan, sailed from Norfolk, Va., on April 9. Baltic, with Fox on board, dropped down to Sandy Hook at the mouth of New York Harbor on the evening of April 8 and put out to sea the following morning.

Almost from the beginning, the weather played havoc with the carefully laid plans. Soon after the steamer Baltic sailed, a heavy gale set in, badly scattering the expedition's vessels and delaying the arrival of Fox's force. When Baltic arrived at Charleston at 3 a.m. on April 12, only Harriet Lane had completed the voyage. By 6 a.m., Pawnee joined the force, but her orders limited her usefulness. Fox boarded the vessel to ask Commander Rowan to stand in toward shore, but the captain could not comply because his orders required him to remain 10 miles east of the lighthouse and await Powhatan's arrival. Meanwhile, the Confederates had opened fire on Fort Sumter at 4:30 a.m. on April 12.

Bad weather was not the only problem plaguing Fox's mission. Complications with her owners prevented the tug Thomas Freeborn from ever sailing from New York. Another tug, Uncle Ben, did sail from New York, only to be seized by the Confederates after the gale drove her to seek shelter at Wilmington, N.C. Of the tugs, only Yankee reached Charleston Harbor, and even her arrival was delayed by rough weather.

Poor communications in Washington proved to be the biggest obstacle to Fox's plan. Fort Sumter was not the only Federal-held fort in Southern territory that was threatened by the Confederates. The strategically vital forts along Florida's Gulf Coast–Fort Taylor at Key West, Fort Jefferson in the Dry Tortugas and Fort Pickens at Pensacola–also required Federal attention. To support those forts, a relief expedition similar to Fox's was being fitted out under the command of Navy Lieutenant David D. Porter. Secretary of State William H. Seward, without the knowledge of Secretary of the Navy Gideon Welles, had obtained Lincoln's authorization to divert Powhatan to the gulf expedition. Just as she was preparing to sail from New York on April 6, Powhatan was ordered to leave the Charleston expedition and was sent to sea as part of the expedition to the Gulf of Mexico.

Powhatan's transfer had a devastating impact on Fox's mission. The Northern warship carried the armed launches and crews necessary to land troops and supplies from Baltic. To make matters worse, Fox did not learn of Powhatan's diversion until April 13, a week after it had taken place.

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