This study examines the interplay between self-regulation, routine-facilitated well-being, and academic stress during wartime among 387 Israeli college and university students. Using a quantitative approach with online questionnaires, the research investigates the mediating role of routine-facilitated well-being and the moderating effects of academic schedule delays, learning environments, gender, academic degree, proximity to war zones, and military reserve service. Findings indicate that self-regulation significantly predicts lower academic stress, with routine-facilitated well-being serving as a mediator. However, maintaining a study routine was also associated with increased stress, suggesting that while routines provide structure, they may impose additional pressures in crisis situations. The study identifies an optimal adaptation window of 6–10 weeks following academic disruptions, where self-regulation has the strongest stress-reducing effect. Hybrid learning environments further enhanced this relationship compared to fully online or face-to-face settings. Differences emerged based on academic degree and gender, with graduate students and women benefiting more from self-regulation through routine-facilitated well-being. Additionally, students in military service experienced greater stress reduction from self-regulation than non-recruited students, while those outside war zones benefited more than those in conflict areas. These findings highlight the need for targeted interventions to support students during crises, emphasizing self-regulation training, adaptive routines, and flexible learning models to enhance resilience under severe stress conditions.