Across the central and eastern United States, upland oaks are experiencing regeneration complications. This thesis comprises two studies evaluating challenges in regenerating upland oaks. One study evaluates upland Quercus spp., Carya spp., and Acer rubrum L. response to prescribed fire and impacts on seedling growth and mortality. This study found prescribed fire promoted oak growth when canopy cover was < 77%. Oaks displayed lower percent mortality and higher resprout capacity after fire compared to red maple. The second study investigates impacts of Microstegium vimineum presence on Quercus alba L., Liriodendron tulipifera L., and Acer rubrum L. seedlings under different light and moisture environments. Microstegium vimineum presence decreased growth of both sweetgum and red maple; white oak was less impacted, likely because of its conservative growth strategy and high-water use efficiency. Oaks’ conservative growth strategy may offer more resiliency compared to its competitors in response to prescribed fire and Microstegium vimineum.