The present study investigated students’ academic procrastination in elementary, secondary, and tertiary education cross-sectionally, by simultaneously examining the predictive role of perceived academic context-related factors and problematic social media use (PSMU) in the manifestation of procrastination. Students from elementary (N = 532), secondary (N = 561) and tertiary education (N = 519) from randomly selected Greek schools and university departments completed a self-report questionnaire, which included scales on academic procrastination, academic engagement, academic connectedness, and PSMU. The results showed that elementary and secondary school students procrastinate more than university students, who perceive procrastination as a problem and desire to reduce it to a greater extent. No gender differences were found regarding students’ procrastination. Furthermore, the path analyses revealed similarities and differences in the explanatory models of procrastination for the three student-groups. Generally, academic engagement and connectedness negatively predicted academic procrastination, while PSMU negatively mediated this relationship. Nevertheless, among the three path models, different dimensions of the predictive variables involved contributed to procrastination in elementary, secondary, and tertiary education. The findings imply that in each level of education specific academic context-related psychological states could be enhanced along with the promotion of safe social media use to effectively prevent students’ academic procrastination.