The transition from high school to university seems to be a tough experience that is likely to result in falling standards and attrition to incoming students. This study seeks to explore preparatory year students' expectations and real experiences at Imam Abdurrahman Bin Faisal University, Saudi Arabia, and to suggest some alternatives to bridge the transition and minimize impediments. A questionnaire of expectations and a questionnaire of experiences were administered to 1955 students and an interview was directed to 245 students. The findings of the study revealed deep discrepancies between students' expectations and experiences and pinpointed that students' academic, social, and logistic needs should be given due consideration to warrant quality and long-life learning