This chapter provides an analysis of a set of conditions that transfer students will most likely face in their transition to a new institution. The specific focus is on transfer from two-year to four-year institutions. This chapter will identify many of the common challenges transfer students face simply because they are entering a new learning environment. It will also provide potential strategies to minimize the shock factor in order to improve transfer students' success, that is, satisfactory completion of their degree, certificate, training, or personal enrichment.