The Highlands–Glades subpopulation (HGS) of Florida, USA, black bears (Ursus americanus floridanus) is small, genetically depauperate, and resides primarily within the endangered Lake Wales Ridge ecosystem, which has lost >85% of native habitat to land development. Habitat loss can reduce availability of critical natural foods and cause bears to increase reliance on anthropogenic foods (i.e., human-sourced); lands supporting the HGS are expected to lose >50% of remaining Florida black bear habitat in coming decades. We used scat analysis to describe seasonal food habits, investigate potential dietary responses to food shortages, and inform habitat conservation and human–bear conflict management. Florida black bears in the HGS mostly relied on native soft and hard mast and invertebrates, which are all available in endangered scrub habitat communities. Corn dispensed at hunter-operated feeding stations was a dominant food item in scats; and other alternative foods, such as citrus fruit and white-tailed deer (Odocoileus virginianus), were found in summer-collected scats when soft mast should have been prevailing. Results indicate bears may respond to soft mast shortages caused by mast failures or habitat loss by consuming anthropogenic foods (e.g., corn, deer chow, citrus fruit, and garbage), which could increase human–bear conflicts. Florida carpenter ants (Camponotus floridanus) appeared to provide a reliable compensatory food during such shortages, but they are arboreal and largely dependent on imperiled bear habitat for proliferation. We strongly suggest remnant scrub and other communities rich in soft and hard mast-producing flora be targeted for acquisition and protection to ensure persistence of Florida black bears in this diverse ecosystem. We also suggest non-lethal actions to mitigate bear habituation to anthropogenic foods be implemented to minimize human–bear conflicts and prevent unnecessary losses to the already small HGS. Our study should be repeated to investigate whether dietary shifts occur in response to impending habitat loss and to further inform population conservation, habitat protection, and conflict management.