Referring to the institutional and research indications, those involved in higher education policies and management are formulating new plans to face, on the one hand, the decline in academic enrolments, on the other, the growing increase of early university-leavers. Academic drop-out and negative experiences and affect, in addition to being indicators of academic ineffectiveness, should be profitably analysed as well as their possible determinants to plan preventive policy measures and strategies. Despite the number of studies that have investigated variables related to learning and study experience, tools have yet to be defined to predict drop-out and delay in academic courses. Starting from the aforementioned assumptions and gaps, and with the aim of predicting academic drop-out and student's negative experiences, an adaptation to the Italian context of the Cynical Attitude Toward College Scale (CATCS) was proposed and its psychometric characteristic analysed through SEM. Moreover, the research investigated the possible role of Student Cynicism in predicting Achievement, and of Student's environmental perceptions in predicting Cynicism. Results showed that the CATCS can be profitably used in the Italian academic context: the CFA of the 11item CATCS version showed that it is a reliable and valid measure.