Drop out is a phenomenon imparted of complexity, factorial polysynthesis, and diversity of consequences unfortunately negative in nature. Thus, a thorough comprehension and analysis of the factors affecting drop out and the tendency to it, are crucial. In this paper, the latter is examined in an effort to enlighten the causes behind the manifestation of drop out so as appropriate interventions are applied. In this respect, the present work focused on those factors that exert direct or indirect influence of positive or negative nature on the way students cope with university studies, overcome obstacles and value the university experience. The research was conducted at the University of Patras on a student sample with 696 valid questionnaires. The findings indicate that the principal factors behind the tendency to drop out are the students’ frustration, the absence from their obligatory academic duties, and dissatisfaction with their cognitive subject. On the contrary, the primary factors decreasing the students’ tendency to drop out are the sense of effectiveness in their studies, the perception of gaining valuable things from studying at university, and the creation of good relationships with their fellow students and university teachers.