The Battle was never supposed to happen.
The Union forces that captured Jacksonville, Florida were ordered to remain in the Jacksonville area to secure it from Confederate forces. However, Union Brigadier General Truman Seymour disobeyed orders and marched towards Tallahassee. During the march along the Florida, Atlantic and Gulf Central Railroad the Union Forces met entrenched Confederate regiments, resulting in a pitched battle.
Brigadier General Truman Seymour greatly underestimated the strength of the Confederate forces at Olustee.
Seymour believed that his Union contingent had encountered small bands of Florida militia and slowly committed the regiments under his command to battle. This was the result of Seymour’s previous successful raids against small pockets of Florida militia which had built up his confidence that there was no serious Confederate threat in Florida.
