Maj. Gen. Stephen D. Lee commanded the Confederate Department of Alabama, Mississippi, and East Louisiana. In early July Lee was in north Mississippi with Forrest. Lee anticipated that the Federals out of Memphis would target Okolona, Mississippi along the Mobile and Ohio Railroad so he prepared to defend it as Maj. Gen. Andrew J. Smith moved deeper into Mississippi.
On July 12, the Federals were in Pontotoc, Mississippi, when Smith made a smart decision. On the morning of the 13th, instead of continuing to Okolona, Smith turned his army due east of Pontotoc and headed for Tupelo, also on the railroad. The Confederates were not prepared to defend Tupelo and scrambled to try and stop the Federals from establishing a strong line on high ground. Forrest's men were unable to prevent Smith's force from taking the advantage. During the night of the 13th, both armies prepared for the battle that would surely rise with the sun the next day.