Biologically rich savannas and woodlands dominated by Pinus palustris once dominated the southeastern U.S. landscape. With European settlement, fire suppression, and landscape fragmentation, this ecosystem has been reduced in area by 97%. Half of remnant forests are not burned with sufficient frequency, leading to declines in plant and animal species richness. For these fire-suppressed ecosystems a major regional conservation goal has been ecological restoration, primarily through the reinitiation of historic fire regimes. Unfortunately, fire reintroduction in long-unburned Longleaf pine stands can have novel, undesirable effects. We review case studies of Longleaf pine ecosystem restoration, highlighting novel fire behavior, patterns of tree mortality, and unintended outcomes resulting from reintroduction of fire. Many of these pineland restoration efforts have resulted in excessive overstory pine mortality (often >50%) and produced substantial quantities of noxious smoke. The most compelling mechanisms of high tree mortality after reintroduction of fire are related to smoldering combustion of surface layers of organic matter (duff) around the bases of old pines. Development of effective methods to reduce fuels and competing vegetation while encouraging native vegetation is a restoration challenge common to fire-prone ecosystems worldwide that will require understanding of the responses of altered ecosystems to the resumption of historically natural disturbances.