Marmaduke's assault ran into trouble quickly and began taking artillery and small arms fire from his left flank. The main attack however, would take place in the center with Sterling Price's 3,100 men seizing Graveyard Hill and the battery protecting it. Walker was assigned the task of guarding Marmaduke's flank and preventing Union reinforcements from reaching Rightor Hill. General Fagan's 1,300 men were assigned to capture Hindman's Hill southwest of the city. Holmes planned for a dawn attack with Marmaduke's 1,700 dismounted cavalry attacking fortified Rightor Hill northwest of the town and capturing the artillery battery stationed there. Union soldiers renamed the town "Hell-in Arkansas". Helena itself was overcrowded with Union troops and was suffering from housing shortages and poor health and sanitation facilities. Union General Prentiss received word that an attack was in the works and actively worked to slow the movement of Confederate forces by felling trees. Holmes and Arkansas governor Harris Flanagin travelled to Helena to take personal command of the attack. Price and Marmaduke would meet up with infantry out of Little Rock, under Brig. Marmaduke would move from Jacksonport, Arkansas, to the vicinity of Helena. Edmund Kirby Smith, commander of the Trans-Mississippi Department, and received permission to attack Helena.
Holmes, commander of the Confederate District of Arkansas, planned a coordinated attack from three sides on the formidable Federal fortifications surrounding Helena in order to relieve pressure on Vicksburg and to prevent Helena being used as a base to attack further into Arkansas.
This transfer left only about 4,000 Union soldiers to protect the Federal enclave at Helena. Just prior to the battle, a large number of troops were transferred to Vicksburg to strengthen the siege around that city. In addition, the USS Tyler, a "timber-clad" gunboat was assigned to support Prentiss. Four artillery batteries with breastworks and rifle pits were placed in a semicircle around the town. Salomon commanded a division from the XIII Corps and had been placed in charge of the forces manning the defenses of Helena, a Mississippi River port town at the terminus of Crowley's Ridge and ringed by steep hills cut by heavily thicketed ravines. Prentiss, in command of the District of Eastern Arkansas, was headquartered at Helena with approximately 20,000 troops.
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