On September 13, 1861, Union and Confederate forces fought the Second Battle of Boonville, roughly halfway in Missouri between St. Louis and Kansas City. It was an otherwise forgettable battle in which 800 Confederate militia under Col. William Brown unsuccessfully tried to surprise a local Unionist militia of only 140 men. The Confederates, protecting their flags against the rain, covered them in black erroneously convincing the Unionists that they intended to give no quarter. Hence, the entrenched Unionists put up a determined resistance despite being badly outnumbered, convinced they were literally fighting for their lives and actually ended up winning the battle, repulsing the Confederate assault.
One of the reasons they won was because they had help from the rebels’ slaves. Buried in the endnotes of Michael Fellman’s Inside War: The Guerrilla Conflict in Missouri During the American Civil War is an interesting excerpt of a letter from a Unionist soldier, Daniel R. Smith. Writing his parents on September 17, 1861, he related:
So were these slaves soldiers? Strictly speaking, no, as they were not enlisted members of formal military unit. They appear to have escaped their owners in the rebel force and sought refuge with the Union militia, bringing them a warning of the impending attack. During the battle, like the Unionists, with nowhere to escape and convinced they would be killed if captured, they fiercely defended themselves. Col. Brown’s slave was lucky to arm himself as his owner approached and exact a personal vengeance. So the slaves’ participation in the Second Battle of Boonville, although informal, for them was a matter of life and death. So they were soldiers there in a viscerally real way, fighting an impromptu battle for their lives. Their service, such as it was, is reminiscent of other incidents during Summer 1861 documented in earlier editions of Civil War Emancipation. See: 1) July 27; 2) July 28; 3) August 1; 4) August 17.
Source: Michael Fellman, Inside War: The Guerrilla Conflict in Missouri During the American Civil War (New York: Oxford University Press, 1989), 280-81.
Civil War Emancipation 
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Emanual Osborn of the St. Augustine Blues (Company E, Third Florida Confederate) was a member in 1861. He was discharged in November 1862 at end of his term of service. Florida Pension records.
I have another one somewhere who was shooting at the Union soldiers at the battle of Bull Run and later became a member of the 33rd or 34th USCT…can’t find my notes on where I got this but if I run into the source I’ll post it.
Was Osborn a mustered in member of the 3rd Florida Confederate or a servant? It’s an important distinction. It was not uncommon for southern states after the Civil War to grant state pensions to “faithful negroes” who had been attached to Confederate units as servants, laborers, teamsters, etc. But NOT as soldiers. – Don
The pension is very careful to avoid any mention of Osborn being African-American. The pension document does not say, but the St. Augustine Blues site lists him as a private. What made this pension interesting was that Osborn’s wife had earlier been married to James Lang of the 33rd. She did not get a divorce from him before marrying Osborn. Her pension for Lang was denied because they ruled it a slave era marriage (which it wasn’t…the St. Augustine Commissioner of Freedmen married them.) that was not continued after slavery. The two pensions attempts accidently fell on each other for me to link them up.