Background Although the effects of early‐onset trauma on susceptibility to psychopathology are well‐acknowledged, no study to date has followed risk and resilience trajectories in war‐exposed young children over lengthy periods and charted predictors of individual pathways. Method In this prospective longitudinal study, we followed 232 children, including 148 exposed to repeated wartime trauma and 84 controls, at three time points: early childhood (1.5–5 years), middle childhood (5–8 years), and late childhood (9–11 years). Children were diagnosed at each time point and four trajectories defined: children exhibiting no pathology at any time point, those displaying early pathology that later remitted, those showing initial resilience followed by late pathology, and children presenting chronic pathology across the entire first decade. Maternal behavioral containment during trauma evocation and child social engagement during free play were observed in early childhood and maternal emotional distress self‐reported across time. Results War‐exposed children showed significantly higher rates of psychopathology, with 81% exhibiting pathology at some point during childhood. In middle childhood, exposed children displayed more posttraumatic stress disorders (PTSD), anxiety disorders, and attention‐deficit/hyperactivity disorders (ADHD), and in late childhood more PTSD, conduct/oppositional defiant disorders, and ADHD. War‐exposed children had more comorbid psychopathologies and number of comorbidities increased with age. Notably, war‐exposure increased prevalence of chronic pathology by 24‐fold. Maternal factors, including mother's uncontained style and emotional distress, increased risk for early and chronic psychopathology, whereas reduced child social engagement augmented risk for late pathology. Conclusions Early‐onset chronic stress does not heal naturally, and its effects appear to exacerbate over time, with trauma‐exposed children presenting a more comorbid, chronic, and externalizing profile as they grow older. Our findings demonstrate that responses to trauma are dynamic and variable and pinpoint age‐specific effects of maternal and child factors on risk and resilience trajectories. Results highlight the importance of conducting long‐term follow‐up studies and constructing individually tailored early interventions following trauma exposure.