Climate change poses many risks to economically and ecologically crucial species. Longleaf pine (Pinus palustris Mill.) trees are keystone species that were once dominant across the southeastern United States, but now occupy less than 5% of their historic range and are thus classified as endangered. Here we review the current status and challenges facing longleaf pine trees, what is known on how changing climate will impact longleaf growth and reproduction, and gaps in the literature that are important to address. We found that many fundamental aspects of longleaf pine growth and reproduction are understood. However, these systems are complex, and not all is known about each factor that influences the relationship between climate, growth, and reproductive output. Additionally, long-term data sets capable of examining all relevant factors in these relationships do not currently exist. To fill necessary gaps, we recommend a joint approach between using readily available data sets and establishing new long-term monitoring plots targeted to collect data on missing or poorly understood conditions. This review provides a clue from an ecological complexity perspective to understand and manage longleaf pine forests under climate change.