Introduction: Early school dropout is a multifactorial phenomenon influenced by academic and school-related aspects. This research aims to determine the influence of variables related to students' school history on premature dropout. Methodology: The study employs a specially developed questionnaire administered to a sample of 1157 secondary education students following both regular and non-regular paths. Descriptive analysis is complemented by multigroup analysis. Results: Findings indicate that schooling path and grade repetition are the two aspects most strongly associated with premature dropout. Additionally, disparities are observed based on school ownership, disruptive behavior, and the presence of specific educational support needs. The main findings suggest that school history substantially influences whether a particular student continues their educational journey. Discussions and Conclusions: Considering these findings, adopting proactive measures aimed at mitigating the impact of potential threatening factors to prevent future early school dropout is proposed, from the perspective of a comprehensive, compensatory, and inclusive education under the paradigm of Universal Design for Learning.