Parents’ early life stressful experiences have lifelong consequences, not only for themselves but also for their children. The current study utilized a sample of military families (n = 266) including data from both active-duty and civilian parents and their adolescent children. Hypotheses reflecting principles of persistence, transmission, and proximity as pertaining to parents and their children were examined. The impact of parents’ childhood experiences on their functioning later in life and, consequently, their adolescent children’s well-being were examined. Adults who encountered more stressful childhood experiences, including relatively prevalent and less severe adversities (e.g., verbal conflict between parents) experienced poorer functioning than adults who encountered little early stress. Civilian parents’ current functioning was related to adolescent children’s well-being, whereas the functioning of active-duty parents was generally not related to children’s well-being. Persistence, transmission, and proximity hypotheses were generally supported but with variations attributable to whether an adult was a military member.