Abstract: Introduction: In light of growing concerns about an increasingly digital adolescence, the academic field investigating how digital technologies affect adolescents’ psychological well-being is growing rapidly. In the last years, much research has amassed, and this has been summarised in over 80 systematic reviews and meta-analyses. Materials and Methods: Systematic reviews, meta-analyses and key studies are reviewed to provide insights into the state of current research linking digital technology and social media use to well-being; possible future directions and improvements are discussed. Results: When examining the reviews, it becomes evident that the research field is dominated by cross-sectional work that is generally of a low quality standard. While research has highlighted the importance of differentiating between different types of digital technology use many studies do not consider such necessary nuances. These limitations aside, the association between digital technology use, or social media use in particular, and psychological well-being is—on average—negative but very small. Furthermore, the direction of the link between digital technology use and well-being is still unclear: effects have been found to exist in both directions and there has been little work done to rule out potential confounders. Conclusions: Reviewing the last decade of reviews in the area, it is evident that the research field needs to refocus on improving transparency, interpreting effect sizes and changing measurement. It also needs to show a greater appreciation for the individual differences that will inherently shape each adolescent’s reaction to digital technologies.