ABSTRACT Introduction More than 90% of children in military families attend civilian schools that may lack understanding of the unique experiences and stressors of military life. School success in children of military families has important implications on future academic achievement, health outcomes, and military groups; yet there has not been an examination of challenges of school success among children of military families in the United States using nationally representative data. Materials and Methods Data captured in the 2021-2022 National Survey of Children’s Health, limited to children aged 6 to 17 years, were used to examine the association between child’s caregiver military status and challenges of school success: lack of school engagement measured through caring about school and completing schoolwork, school absenteeism, and grade repetition (n = 60,599). Weighted to be nationally representative, bivariate analyses used chi-squared tests to examine estimates between selected variables and caregiver military status. Multivariable regression analyses were used to examine the association between caregiver military status and challenges of school success measures. Results In both unadjusted and adjusted analyses, we found that children of military families were more likely to not be engaged in school (adjusted odds ratios 1.35; 95% CI 1.19–1.53) and more likely to repeat a grade (adjusted odds ratios 1.33; 95% CI 1.09–1.64) than their civilian counterparts. There were no statistically significant differences in school absenteeism between children of military families and of civilian families. Conclusions This study extends beyond previous research findings that have focused primarily on academic achievement by including school engagement, attendance, and grade repetition for a more holistic and complete understanding of school success of children in military families. Our findings can be informational for school systems and policymakers to create educational and connective interventions for children in military families to improve school success.