The present study examined individuation and expectations for autonomous behavior (EAB) with incoming college freshmen and their parents. To test the theory that greater mismatch between young adults and their parents about EAB would be associated with more negative adjustment to college, Collins' (1990) Expectancy-Violation Model was applied. Data were initially collected with online questionnaires from incoming college freshmen and one of their parents before the transition to college. Follow-up data (W2) were collected three months later to assess adjustment to college. Individuation was measured with the Late Adolescence Individuation Questionnaire; EAB and reports of actual autonomous behavior were assessed with a measure based on the Psychological Separation Inventory. College student adjustment was measured with indicators of psychological well-being (i.e., psychosomatic symptoms, depressive symptoms, positive affect) and adaptation to college (i.e., college self-efficacy, satisfaction with college, and anticipated fall college grades). Open-ended data were collected from young adults and their parents describing topics of autonomy behavior where they perceived disagreement. A MANOVA indicated that there were significant differences between the four individuation groups (a) individuated (high connectedness and high separateness), (b) pseudoautonomous (low connectedness and high separateness), (c) dependent (high connectedness and low separateness), and (d) ambiguous (low connectedness and low separateness) on the young adults' adjustment to college. Post-hoc planned comparisons revealed that college students in the "individuated" group were consistently better off than those in the "ambiguous" group. Some support was found for the hypothesis that a higher discrepancy (a) between parent and young adult EAB and (b) between young adults' reports of expected versus actual autonomous behaviors was associated with lower W2 young adult well-being. Quality of parent-young adult communication was found to moderate some of these associations. Qualitative data somewhat supported the quantitative results, as well as illustrated unique areas for disagreement on EAB. Jointly, these quantitative and qualitative findings suggest that young adults' level of individuation from parents and a mismatch between parents' and young adults' perceptions of future autonomous behavior may impact college students' psychological well-being during the transition to college.