This study begins with an attempt to identify the characteristics of the digital generation and continues with Prensky’s pioneering distinction between digital natives and digital immigrants. Then, the study focuses on the digital generation’s relationship with the university and the extent to which technology affects their performance. This is followed by a presentation of research studies that suggest that members of this generation are less open to the use of technology. Further, research evidence is presented on the negative correlation between social media use and academic performance, and that most young people today, although familiar with the use of digital tools, still need guidance to develop critical thinking skills. The study then focuses on the relationship between the digital generation and school and the extent to which technology affects their performance. Studies show that the use of technology in the educational process can have a positive impact on students’ motivation and performance, but other studies show that the excessive use of technology, especially for extracurricular purposes, can negatively affect performance, distract attention and concentration, while the risk of social isolation and marginalisation of students is not absent. This study concludes with the challenges and stakes that are currently being created for the Greek school.