Steuart was promoted to brigadier general on March 6, 1862, commanding a brigade in Major General Richard S. Ewell's division during Stonewall Jackson's Shenandoah Valley campaign. On May 24 Jackson gave Steuart command of two cavalry regiments, the 2nd and 6th Virginia Cavalry regiments. At the First Battle of Winchester, on May 25, 1862, Jackson's army was victorious, and the defeated Federal infantry retreated in confusion. The conditions were now perfect for the cavalry to complete the victory, but no cavalry units could be found to press home the advantage. Jackson complained: "never was there such a chance for cavalry! Oh that my cavalry were in place!" The exhausted infantry were forced forward again, while Lieutenant Sandie Pendleton of Jackson's staff was sent to find Steuart.