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On May 10, Union engineers discovered a potential weakness in the Confederate fortifications. On the western edge of the salient, at an outward bend in the line, the enemy field of fire was limited due to the proximity of the Union-held wood line, which could also be used for cover. Colonel Emory Upton, a smart and energetic, 24-year-old 1861 West Point graduate from New York, won approval to lead a compact attack formation of 12 hand-picked regiments, about 4,500 men total, to assault the Confederates there in the brigade of Brig. Gen. George Doles. Upton believed a solid, fast moving blow might effectively penetrate the enemy line to be exploited by follow-on attacking elements.

Upton’s column was four lines of three regiments abreast. Lead regiments would peel off left and right after breaching the line to clear the works. Upton’s former regiment, the 121^st New York Infantry, was in the first rank. Upton formed his column just inside the woods and at 6:30 p.m., after a half-hour artillery bombardment, attacked. Upton’s men covered the 200 yards of open ground between the woods and Doles’ line in a matter of seconds.

Attacking with only the bayonet, they swept over the works, scooping up 1,000 prisoners, before pressing on and capturing a second line of works. Lee immediately counterattacked, forcing Upton’s men to take cover. Other attacks that were supposed to draw Confederate attention away from Upton’s column fizzled early. Not properly supported, Upton’s men were beaten back, losing around 1,000 men. Impressed anyway, Grant promised “a brigade today, we’ll try a corps tomorrow.”