As the Union troops dug in around Chancellorsville that night, creating log breastworks, faced with abatis, Lee and Stonewall Jackson met at the intersection of the Plank Road and the Furnace Road to plan their next move. Jackson believed that Hooker would retreat across the Rappahannock, but Lee assumed that the Union general had invested too much in the campaign to withdraw so precipitously. If the Federal troops were still in position on May 2, Lee would attack them. As they discussed their options, cavalry commander J.E.B. Stuart arrived with an intelligence report from his subordinate, Brig. Gen. Fitzhugh Lee.^[5]

Although Hooker's left flank was firmly anchored by Meade's V Corps on the Rappahannock, and his center was strongly fortified, his right flank was "in the air." Howard's XI Corps was camped on the Orange Turnpike, extending past Wilderness Church, and was vulnerable to a flanking attack. Investigations of a route to be used to reach the flank identified the proprietor of Catharine Furnace, Charles C. Wellford, who showed Jackson's cartographer, Jedediah Hotchkiss, a recently constructed road through the forest that would shield marchers from the observation of Union pickets. Lee directed Jackson to make the flanking march, a maneuver similar to the one that had been so successful prior to the Second Battle of Bull Run (Second Manassas). An account by Hotchkiss recalls that Lee asked Jackson how many men he would take on the flanking march and Jackson replied, "my whole command."^[5]