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Hooker took advantage of improved military intelligence about the positioning and capabilities of the opposing army, superior to that available to his predecessors in army command. His chief of staff, Butterfield, commissioned Col. George H. Sharpe from the 120th New York regiment to organize a new Bureau of Military Intelligence in the Army of the Potomac, part of the provost marshal function under Brig. Gen. Marsena R. Patrick. Previously, intelligence gatherers, such as Allan Pinkerton and his detective agency, gathered information only by interrogating prisoners, deserters, "contrabands" (slaves), and refugees. The new BMI added other sources including infantry and cavalry reconnaissance, spies, scouts, signal stations, and an aerial balloon corps. As he received the more complete information correlated from these additional sources, Hooker realized that if he were to avoid the bloodbath of direct frontal attacks, which were features of the battles of Antietam and, more recently, Fredericksburg, he could not succeed in his crossing of the Rappahannock "except by stratagem."

Hooker's army faced Lee across the Rappahannock from its winter quarters in Falmouth and around Fredericksburg. Hooker developed a strategy that was, on paper, superior to those of his predecessors. He planned to send his 10,000 cavalrymen under Maj. Gen. George Stoneman to cross the Rappahannock far upstream and raid deep into the Confederate rear areas, destroying crucial supply depots along the railroad from the Confederate capital in Richmond to Fredericksburg, which would cut Lee's lines of communication and supply. Hooker reasoned that Lee would react to this threat by abandoning his fortified positions on the Rappahannock and withdrawing toward his capital. At that time, Hooker's infantry would cross the Rappahannock in pursuit, attacking Lee when he was moving and vulnerable. Stoneman attempted to execute this turning movement on April 13, but heavy rains made the river crossing site at Sulphur Spring impassable. President Lincoln lamented, "I greatly fear it is another failure already." Hooker was forced to create a new plan for a meeting with Lincoln, Secretary of War Edwin M. Stanton, and general in chief Henry W. Halleck in Aquia on April 19.

Hooker's second plan was to launch both his cavalry and infantry simultaneously in a bold double envelopment of Lee's army. Stoneman's cavalry would make a second attempt at its deep strategic raid, but at the same time, 42,000 men in three corps (V, XI, XII Corps) would stealthily march to cross the Rappahannock upriver at Kelly's Ford. They would then proceed south and cross the Rapidan at Germanna and Ely's Ford, concentrate at the Chancellorsville crossroads, and attack Lee's army from the west. While they were under way, 10,000 men in two divisions from the II Corps would cross at the U.S. Ford and join with the V Corps in pushing the Confederates away from the river. The second half of the double envelopment was to come from the east: 40,000 men in two corps (I and VI Corps, under the overall command of John Sedgwick) would cross the Rappahannock below Fredericksburg and threatened to attack Stonewall Jackson's position on the Confederate right flank. The remaining 25,000 men (III Corps and one division of the II Corps) would remain visible in their camps at Falmouth to divert Confederate attention from the turning movement. Hooker anticipated that Lee would either be forced to retreat, in which case he would be vigorously pursued, or he would be forced to attack the Union Army on unfavorable terrain.

One of the defining characteristics of the battlefield was a dense woodland south of the Rapidan known locally as the "Wilderness of Spotsylvania". The area had once been an open broadleaf forest, but during colonial times the trees were gradually cut down to make charcoal for local pig iron furnaces. When the supply of wood was exhausted, the furnaces were abandoned and secondary forest growth developed, creating a dense mass of brambles, thickets, vines, and low-lying vegetation. Catharine Furnace, abandoned in the 1840s, had recently been reactivated to produce iron for the Confederate war effort. This area was largely unsuitable for the deployment of artillery and the control of large infantry formations, which would nullify some of the Union advantage in military power. It was important for Hooker's plan that his men move quickly out of this area and attack Lee in the open ground to the east. There were three primary roads available for this west-to-east movement: the Orange Plank Road, the Orange Turnpike, and the River Road.

The Confederate dispositions were as follows: the Rappahannock line at Fredericksburg was occupied by Longstreet's First Corps division of Lafayette McLaws on Marye's Heights, with Jackson's entire Second Corps to their right. Early's division was at Prospect Hill and the divisions of Rodes, Hill, and Colston extended the Confederate right flank along the river almost to Skinker's Neck. The other division present from Longstreet's Corps, Anderson's, guarded the river crossings on the left flank. Stuart's cavalry was largely in Culpeper County near Kelly's Ford, beyond the infantry's left flank.