The aim of this study was to investigate the influencing factors of successfully rescuing year-round housed cattle in case of a barn fire. Empirical research indicates the reluctance of cattle to leave their familiar barn. Subsequent retreat back to the perceived safety inside, which stands in contrast to the unknown and thus adversary elements outside, for example, the fire brigade, is to be expected. We examined the evacuation of 69 dairy cattle, split into three groups, to an adjacent pasture by night and inspected the animals’ acceptance of two differently designed escape routes and the effect of preceding training. Along with the time needed for evacuating all animals, we measured faecal cortisol metabolites and daily milk yield to assess stress in the animals. Our preliminary assumption was that cattle trained for pasture would have a decisive advantage over untrained cattle. However, adapting the exits to the sensory physiology of the cattle resulted in an extensive impact on the animals’ readiness to leave the familiar housing, as the evacuation of the cattle non-habituated to the exit was comparatively quick and successful. We consider this study instructional for fire brigades and farmers, encouraging them to develop a customised concept for rescuing their cattle in case of an emergency.