Human–wildlife interactions are increasing in severity due to climate change and proliferating urbanization. Regions where human infrastructure and activity are rapidly densifying or newly appearing constitute novel environments in which wildlife must learn to coexist with people, thereby serving as ideal case studies with which to infer future human–wildlife interactions in shared landscapes. As a widely reviled and behaviorally plastic apex predator, the spotted hyena (Crocuta crocuta) is a model species for understanding how large carnivores navigate these human‐caused ‘landscapes of fear’ in a changing world. Using high‐resolution GPS collar data, we applied resource selection functions and step selection functions to assess spotted hyena landscape navigation and fine‐scale movement decisions in relation to social–ecological features in a rapidly developing region comprising two protected areas: Lake Nakuru National Park and Soysambu Conservancy, Kenya. We then used camera trap imagery and Barrier Behavior Analysis (BaBA) to further examine hyena interactions with barriers. Our results show that environmental factors, linear infrastructure, human–carnivore conflict hotspots, and human tolerance were all important predictors for landscape‐scale resource selection by hyenas, while human experience elements were less important for fine‐scale hyena movement decisions. Hyena selection for these characteristics also 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' semi‐permeable electric fences as risky but may cross them out of necessity. Our findings highlight that the ability of carnivores to flexibly respond within human‐caused landscapes of fear may be expressed differently depending on context, scale, and climatic factors. These results also point to the need to incorporate societal factors into multiscale analyses of wildlife movement to effectively plan for human–wildlife coexistence.