Research examining the relationship between social support and psychological well-being has largely ignored the negative side of social interactions. However, empirical evidence suggests that negative interactions can potentially be more harmful than social support is helpful. This article critically reviews the literature investigating the relationship between social support and negative social interactions and their simultaneous effect on psychological well-being. A review of 28 studies revealed that there are conceptual, theoretical, and methodological limitations associated with this body of research. In order to unravel some of these limitations, studies are grouped according to three conceptual models: the additive effects model, the moderator model, and the domain-specific model. Finally, the article discusses directions social work practice research should take to tackle and fully appreciate the complexities of the relationship between social support and psychological well-being.