The question of whether and how digital media use and digital communication affect people’s and particularly adolescents’ well-being has been investigated for several decades. Many studies have analyzed how different forms of digital communication influence loneliness and life satisfaction, two comparatively stable cognitive indicators of subjective well-being. Despite this large body of empirical work, the findings remain ambivalent, with studies resulting in positive, negative, or nonsignificant effects. Several meta-analyses suggest that the overall effect of digital communication on life satisfaction is probably too small to suggest a detrimental effect. The net effect of digital communication on loneliness, by contrast, is positive, but likewise small. Yet the studies on which these meta-analyses are based suffer from several limitations. They often adopt a limited perspective on the phenomenon of interest as a disproportionate amount of work focuses on interpersonal differences instead of intra-individual, contextual, and situational effects, as well as their interactions. Furthermore, studies are often based on cross-sectional data, use unvalidated and imprecise measurements, and differ greatly in how they conceptualize digital communication. The diversity in studied applications and forms of digital communication also suggests that effects are most likely bidirectional. Passive digital communication (e.g., browsing and lurking) is more likely to result in negative effects on well-being. Active and purposeful digital communication (e.g., posting, liking, conversating), by contrast, is more likely to result in positive effects. Future research should therefore investigate how the various levels of digital communication (including differences in devices, applications, features, interactions, and messages) interact in shaping individuals’ well-being. Instead of expecting long-term effects on comparatively stable cognitive indicators such as life satisfaction, scholars should rather study and identify the spatial and temporal boundaries of digital communication effects on the more fluctuating affective components of well-being.