The mounted raiders achieved complete surprise, capturing the Federal garrison and destroying $1.5 million of supplies intended for Ulysses S. Grant's army.

Additionally, both Van Dorn and Forrest's raids obstructed the full implementation of Grant's controversial General Order No.

After Van Dorn's defeat in the Second Battle of Corinth on October 3–4, 1862, Confederate President Jefferson Davis named John C. Pemberton to lead the Department of Mississippi and East Louisiana and elevated him in rank to Lieutenant General.

[2] As he awaited approval from Union General-in-chief Henry Halleck, Grant began concentrating five divisions at Grand Junction, Tennessee.

Though a recent prisoner exchange swelled Van Dorn's strength to 24,000 troops, many of his soldiers were in poor health and the onset of cold weather increased the sick list.

[5] Van Dorn retreated behind the Yalobusha River covering Grenada, only 120 mi (193 km) north of Vicksburg.

[4] At this time, Lieutenant Colonel John S. Griffiths of the 6th Texas Cavalry Regiment suggested raiding Grant's supply base at Holly Springs.

[4] Meanwhile, President Abraham Lincoln authorized John A. McClernand to raise an army in the Midwestern states and lead it in an expedition against Vicksburg.

After passing New Albany, the raiders swung west and rested 12 to 15 mi (19 to 24 km) from Holly Springs in the evening.

[5] The Union commander of Holly Springs, Colonel Robert C. Murphy of the 8th Wisconsin Volunteer Infantry Regiment, was warned that a Confederate force was at large, but he failed to alert his garrison.

Following up his success, Van Dorn continued moving north along the railroad toward Bolivar, capturing Union soldiers posted along the line and wrecking the track and bridges.

The only check to Van Dorn's progress occurred at Davis' Mills where Colonel W. H. Morgan and 300 Union soldiers guarded a trestle bridge across the Wolf River.

The raiders evaded a Federal pursuit column south of Ripley, Mississippi and returned safely to Grenada on December 28.

[10] As historian Shelby Foote described it, "Van Dorn having destroyed his supplies on hand and Forrest having made it impossible for him to bring up any more," Grant was compelled to retreat.

In order to feed his soldiers, the Union general sent out escorted wagons to take food and forage from a swath 15 mi (24 km) wide on either side of the railroad line.

Additionally, Confederate General Nathan Bedford Forrest's West Tennessee Raids, starting December 10, destroyed communications along fifty miles of the Mobile and Ohio Railroad behind Grant's front line.

It took 11 days for the order to reach Paducah, Kentucky, after which local Jewish leaders appealed directly to President Abraham Lincoln.