Dental trauma is highly prevalent, involving 25% of school-age children and about 12.5% of the general population of the world. Due to the young age of the patients that are usually involved in dental trauma, there are tooth-related complicating factors, such as open apices, thin dentinal walls, and unfavorable crown-to-root ratio, as well as patient-related factors, such as anxiety and cooperation, and other challenges related to the complex diagnosis and treatment. Therefore, it is not surprising that the global status of knowledge for the prevention and emergency management of traumatic dental injuries among dental professionals was often reported as insufficient. Aiming to improve dental trauma education, one should consider that the contemporary educational settings have transitioned to a digital learning ecosystem and that the current students belong to a unique generational cohort. Therefore, this paper examines the challenges educators encounter in contemporary dental school classrooms and the defining characteristics of current generation Y and Z dental student cohorts. Finally, it outlines strategies to optimize dental trauma learning, considering the unique generational characteristics of the current dental students.