The impact of consecutive natural events on educational outcomes was analyzed using the case study of Puerto Rico. It explains how interruptions in school service linked to Hurricane Maria and the earthquake sequence of 2020 affected academic performance, especially in vulnerable populations. The data comes from a variety of databases and includes individual student information. Empirical analyses include the difference in differences (DD) method, the Heckman—Copula estimate, Propensity Score Pairing, Cox and Weibull duration regressions, and the Ordinary Least Squares (OLS) method. Our findings suggest that students in severely affected areas, or whose school was permanently closed after the hurricane, are more likely to decrease their academic performance and, in certain cases, to drop out of school after the disaster. It concludes with public policy recommendations to strengthen the capacity to respond to school interruptions caused by hurricanes, floods or earthquakes.