Two studies conducted in an Italian middle school investigated the use and effectiveness of deadlines in improving students’ time management. In Study 1, the setting of deadlines was manipulated: students had to complete 3 tasks and they were asked to submit their work either all at the end of the study (Final condition), or one task at a time at regular intervals (Regular condition), or to set autonomously a deadline for each task (Autonomous condition). In Study 2, there were again 3 tasks and all students had to complete each of them at regular intervals, while we manipulated who would suffer the consequence of a delayed delivery: either the same student responsible for the delay (Self condition), or another student; in the latter case, the victim would either know (Other Disclosure condition) or ignore (Other Anonymous condition) the identity of the culprit. Results show that middle school students try to use deadlines strategically to improve time management, yet they largely fail to obtain the desired results. Moreover, past school performance is found to strongly correlate with effectiveness in time management, and interesting gender differences are observed in the degree of and motivation for deadline compliance