This chapter presents an overview of the psychological adjustment challenges of first-year students. A review of the literature has been carried out to address the main research question of this study: “What are the psychological adjustment challenges that first-year university students face?” The chapter discusses the most common factors that negatively affect adjustment to universities such as stress, anxiety and fears, depression, self-esteem, the importance of self-esteem, signs of high and low self-esteem, and the coping strategies used by first-year university students in the university transition adaptation process. The chapter recommends university authorities initiate stress management programmes such as expanding counselling activities and providing adequate facilities and resources at the campus. Similarly, efficient advisory mechanisms and extracurricular activities and psychological and academic counselling services should be geared toward the needs of the students.