This article presents a model of interaction of personal and contextual variables in the prediction of academic performance and psychosocial development of Portuguese college students. The sample consists of 560 first-year college students of the University of Minho. The path analysis results suggest that initial expectations of the students' involvement in academic life constituted an effective predictor of their involvement during their first year; as well as the social climate of the classroom influenced their involvement, well-being and levels of satisfaction obtained. However, these relationships were not strong enough to influence the criterion variables integrated in the model (academic performance and psychosocial development). Academic performance was predicted by the high school grades and college entrance examination scores, and the level of psychosocial development was determined by the level of development showed at the time they entered college. Though more research is needed, these results point to the importance of students' pre-college characteristics when we are considering the quality of their college adjustment process.