A growing body of research points to the value of multiple group memberships for individual well-being. However, much of this work considers group memberships very broadly and in terms of number alone, and in so doing, advances an argument that when it comes to group memberships, more is better. We conducted five studies to delve further into this idea. Specifically, across these studies we considered how different features of groups may impact on how group memberships combine with one another and affect individual well-being. In two correlational studies, we found that multiple group membership indeed contributed to well-being, but also that this effect was moderated by the distinctiveness of those groups within the overall self-concept (Study 1), and by the social value and visibility of individual group memberships (i.e., stigma; Study 2). In both studies, these effects were mediated by perceived access to social support and by the reported ability to engage in identity expression (i.e., to communicate to others who one “really is”). Across another three studies we experimentally demonstrated that multiple group membership increased well-being and resilience to stress (Study 3 and 4), but only when the given groups were perceived as compatible in nature (Study 3 and 5). Together, these studies suggest that the benefits of multiple group membership depend on factors that go beyond their sheer number. Indeed, the content and social meaning of group memberships, individually and in combination, and the way in which these features guide self-expression and social action, determine whether multiple group memberships are a benefit or a burden for individual well-being and resilience.