Abstract Purpose of Review The neuroendocrine stress response is a natural process of our body which, however, might become toxic if not properly turned on and off. Resilience is the ability to adapt to adverse situations and, particularly, to cope with uncontrolled stress. Resilience and stress are two opposite faces of the same coin, and both are deeply linked to sleep: low resilience means higher stress and, through that, more sleep disorders. The aim of the present paper is to review the complex relationship between these actors and to highlight the possible positive role of good sleep in contrasting chronic stress situations. Recent Findings Promotion of cognitive-behavioral therapy for insomnia patients improves sleep quality and, through that, produces lower general stress, lower depressive symptom severity, and better global health. Summary Sleep is a modifiable behavior and, according to recent studies, its improvement might enhance resilience and, in turn, reduce stress.