To address a gap in the literature we examined sibling relationships as a context for positive development. Specifically, the relationships between individual well-being, sibling closeness, and frequency of sibling communication were explored. The goal of this study was to determine whether individual well-being moderated the relationship between frequency of sibling communication and perceived sibling closeness. Participants included a subsample (n = 236) of youth from a larger study who reported having at least one sibling. Data were collected through Amazon’s Mechanical Turk. Hierarchical multiple regression analyses revealed that associations between frequency of sibling communication and sibling closeness were statistically significant, sibling communication and closeness were highly correlated, regardless of individual differences. Neither emotional, psychological, nor social well-being moderated the relationship between frequency of sibling communication and sibling closeness. Limitations and future directions are considered.