Little is known about what predicts student service members’ and veterans’ (SSM/V) adjustment to college. In qualitative research, SSM/V report feeling they do not belong and are misunderstood by college communities, a phenomenon that counseling psychologists call cultural incongruity. The goal of the current study was to quantitatively examine the relationship between cultural incongruity and adjustment to college. We surveyed 814 SSM/V about their adjustment to college using the Student Adaptation to College Questionnaire. Cultural incongruity was operationalized in two ways: feelings of not belonging were measured via direct report and the association with adjustment to college assessed with regression. Feelings of being misunderstood about academic barriers were assessed by comparing SSM/V’s perceptions of academic barriers and SSM/V’s perceptions of how others view the SSM/V’s academic barriers and the association with adjustment was assessed using polynomial regression and response surface analysis. Cultural incongruity predicted adjustment to college. After controlling for other known predictors, feelings of not belonging accounted for 18% of the variance in adjustment to college. Polynomial regression showed that feeling understood about academic barriers protected against the negative impact of the barrier on adjustment to college. Cultural incongruity predicts adjustment to college for SSM/V. Helping SSM/V feel their unique barriers to college adjustment are understood may blunt the impact of these barriers.