 Ramba uchinyora ndima iyi - Pakutanga kweHondo Yenyika yeAmerica, Omohundro akaedza kubatana nomukoma wake, Orville, muuto reConfederate. Akarambwa kaviri nokuda kwezera rake, asi akabvumirwa kushanda somutumwa padzimbahwe reVirginia Militia pasi paMajor General John B. Floyd. Nemhaka youduku hwake nezivo yomumaruwa, akazivikanwa seBoy Scout weConfederation. MunaFebruary 1864, pazera remakore gumi nemanomwe, akabudirira kunyoresa sevanhu muKambani G ye5th Virginia Cavalry, chikamu cheHondo yeNorthern Virginia, uye munguva pfupi yakanga ichishandira zvakananga muGeneral J.E.B. Stuarts command semutumwa uye scout. Muhondo yeYellow Tavern, akaendesa mushumo wokuongorora kuna Stuart maminitsi mashomanana chete mukuru wacho asati aurayiwa muhondo. Mukati meHondo yeTrevilian Station, Omohundro akakuvadzwa ndokupinzwa muConfederate States General Hospital muCharlottesville musi waJune 20, 1864. Mushure mokupora kubva mukukuvadzwa kwake, uye nguva pfupi yekusiya musha, akadzokera kukambani yake uye akaongorora pasi pehutungamiri hweGeneral Lunsford L. Lomax. Pashure peHondo yechitatu yeWinchester, 5th Virginia Cavalry yakabatanidzwa ne15th Virginia Cavalry, uko Omohundro akaongorora pasi peGeneral Fitzhugh Lee mumwedzi yekupedzisira yehondo. 