A prevailing notion in the literature on workplace gossip is that positive gossip generates benefits for the gossip target. We challenge this notion by examining the relationship between daily positive gossip about a coworker, the gossip sender’s daily envy towards the coworker, and the gossip sender’s subsequent interpersonal interactions with that coworker. Drawing upon the literature on the dual nature of envy, we propose that engaging in higher levels of daily positive gossip is positively related to the gossiper’s daily experiences of both benign envy and malicious envy, which in turn motivates the gossiper to engage in helping behavior and social undermining behavior towards the gossip target at that day, respectively. Additionally, we posit that the positive indirect effect of positive gossip about a coworker on helping (versus social undermining) via benign (versus malicious) envy is stronger for employees with lower (versus higher) moral disengagement. Results from two studies utilizing experience sampling method (ESM) largely supported our research model, except for the moderation of moral disengagement on the positive gossip – benign envy relationship. Finally, we discuss the theoretical and practical implications of our findings.