“Coexistence frontiers”, or regions where human infrastructure and activity are increasing rapidly or newly appearing, constitute novel environments where wildlife must learn to navigate and coexist with people. It is widely recognized that behaviorally flexible species are more likely to persist in these human-dominated landscapes. Nevertheless, we do not fully understand how these animals navigate landscapes shaped by infrastructure, human activity, and human tolerance. As a widely reviled and behaviorally plastic apex predator, the spotted hyena (Crocuta crocuta) is a model species for understanding how wide-ranging large carnivores navigate social-ecological landscapes in an urbanizing world. Using high-resolution (minimum 5-min fix rates) GPS collar data and supplemental camera trap imagery, we applied resource selection and step selection functions to assess spotted hyena landscape navigation and fine-scale movement decisions in relation to social-ecological features in Lake Nakuru National Park and Soysambu Conservancy, Kenya. Second, we used camera traps and barrier behavior analysis (BaBA) to further examine hyena interactions with barriers. Our results show that environmental covariates—including NDVI, terrain, and proximity to water—were the best predictors of landscape-scale resource selection by hyenas, while human infrastructure and the likelihood of conflict with humans or livestock predicted fine-scale hyena movement decisions. We also found that hyena selection for these characteristics changed seasonally and across land management types. Camera traps documented an exceptionally high number of individual spotted hyenas (234) approaching the national park fence at 16 sites during the study period, and BaBA results suggested that hyenas perceive protected area boundaries’ electric fences as risky but may cross them out of necessity. Our results highlight that wildlife adaptability in coexistence frontiers may be expressed differently depending on context and scale. These results also point to the need to incorporate societal factors into multiscale analyses of carnivore movement to effectively plan for human-carnivore coexistence.