After the Civil War ended, Yount became engaged to Estella Braun, a Western Union employee in Detroit, Michigan. She was killed in a train wreck before their wedding could take place, and he never married. Yount traveled to Fort Kearny, along the Oregon Trail in Nebraska. There he was hired as an Army bullwhacker, transporting supplies by wagon along the Bozeman Trail between Fort Laramie in modern-day Wyoming and Fort C.F. Smith in modern-day Montana. There was conflict with Native Americans in this region in those years, and Yount fought against Cheyenne and Sioux warriors several times while on the trail. In one incident, his ox wagon was harassed for four days by a party of Sioux warriors, until he fired his carbine at one warrior, hitting and probably killing the warrior's horse. Supernaugh comments that Yount believed that Indians would kill him if they could, but that he did not "blame the Indians for defending what was their country originally." Yount also worked as a buffalo hunter during this period. He sold buffalo tongues for $1 each to tourists in Cheyenne. Yount believed that "it was a pity to kill off the buffaloes, which were here in immense numbers, but it was the only way to get rid of the Indians, as the buffalo were their main source of subsistence."