Longleaf pine (Pinus palustris Mill.) is a conifer historically associated with an open forest ecosystem that extended across much of the coastal plain of the Southeastern United States. It now exists mainly in isolated fragments following the conversion of forests and the long-term disruption of the low-intensity fire regime upon which the species depends. Recent decades have seen efforts to restore longleaf pine forests by government and private landowners. This was reflected in analyses of national forest inventory data during two time periods, ca. 2009–2015 and 2016–2021, that showed increases in the estimated number of longleaf pine trees, the area of the longleaf pine forest type, and the number and area of planted longleaf pine, along with growth in mean plot-level longleaf pine carbon and importance value. At the same time, we found a decrease in the overall forest area containing longleaf pine, manifested across a variety of other forest types. These results point to a dynamic through which forests dominated by longleaf pine are becoming more widespread via restoration, while forests in which the species is a less important component are transitioning to other forest types or land uses. We also detected a decrease over time in the estimated number of longleaf seedlings across most states and forest types and a decline in naturally regenerated longleaf pine. To further assess regeneration trends in longleaf pine, we calculated the estimated proportion of small trees (seedlings and saplings) for the entire species and for seed zone sub-populations. We found a species-wide decrease in the proportion of small trees, from 82.1 percent to 75.1 percent. This reduction was most pronounced along the edges of the species distribution and could indicate less sustainable levels of regeneration in some areas. These results underscore the challenges of facilitating natural regeneration in this important species.