While Grant's pressure had kept Lee fully occupied at Petersburg, Military affairs elsewhere in the Confederacy had gone from bad to worse. Following his capture of Atlanta, General William T. Sherman had conceived and carried out his "march to the sea," which brought his armies into Savannah, Georgia, on December 21. After a brief pause to regroup, Sherman had marched north into the Carolinas, fought and won a major battle at Bentonville, North Carolina, on March 19 and 20, and was encamped around Goldsboro awaiting dry roads to continue toward Richmond. Confronting him, but barely opposing him, was all that remained of a once powerful Confederate western army, now led by Gen. Joseph E. Johnson.
In the Shenandoah, Sheridan had crushed the Rebel Army of the Valley at Cedar Creek on October 19 and spent the next months consolidating Union control in the region. Satisfied that there was no longer any threat there, Sheridan brought his powerful army back to Petersburg and rejoined Grant in late march.
With Sheridans arrival, Grant had the mobile striking force he needed to end the siege. He worried that Lee would still find a way to slip out of Petersburg and march south to unite with Johnson, so he was eager to cut off Lee's best route in that direction, the South Side Railroad. To accomplish this, Sheridan was instructed to advance west from the Union lines to Dinwiddie Court House on the Boydton Plank Road. From there he would ride north for eight miles to reach the railroad tracks. While Sheridan was moving, Federal infantry would also march to the west to secure the Boydton Plank Road below Burgess' Mill and to challenge the enemy's entrenchments dug along the White Oak Road.
The infantry, Warren's Fifth Corps, made contact first and engaged Lee's men in some sharp fighting along the plank road on March 29. A large scale followup action on March 31 moved the Federal infantry closer to Lee's White Oak Road line, but the position itself remained in Confederate hands. This proved to be a touch-and-go affair, with several of Warren's divisions routed by much smaller Rebel units before reinforcements stabilized the situation.
Sheridan, on March 31, fought a daylong battle around Dinwiddie Court House. His movement had been reported to Lee, who dispatched a force of infantry under Major General George E. Pickett and cavalry led by Major General Fitzhugh Lee. The two proved to much for Sheridan's men, who, by nightfall, had been pressed back to a tight perimeter around the village. Sheridan's call for help was answered by Grant, who ordered the nearest infantry to come to his aid.
Sheridan reported directly to Grant, while Warren took his orders from Meade (who got them from Grant), so there was some delay and miscommunication as Warren carried out his new instructions. His march toward Sheridan was detected by Pickett, who, fearing the enemy would get to his rear, pulled back. Pickett wanted to take a position behind Hatcher's Run, but Lee ordered him to halt short of that point to protect a key road junction known as Five Forks.