Gossip is pervasive at the workplace, yet receives scant attention in the sensemaking literature and stands on the periphery of organization studies. We seek to reveal the non-triviality of gossip in processes of sensemaking. In drawing on empirical data from an observational study of a British Media firm, we adopt a processual perspective in showing how people produce, understand, and enact their sense of what is occurring through gossip as an evaluative and distinct form of informal communication. Our research draws attention to the importance of gossip in the routines of daily practice and the need to differentiate general from confidential gossip. We discuss how gossip continuously informs learning as evaluative sensemaking processes that encourages critiques and evaluation to shape future action and behavior. Within this, we argue how confidential gossip can challenge power relations while remaining part of formal authority structures, constituting forms of pragmatic and micro-resistance. This shadowland resistance provides terrain for learning that both criticizes and preserves espoused values and cultural norms. We conclude that confidential gossip as an evaluative and secretive process provokes a learning paradox that both enables and constrains forms of resistance in reinforcing and simultaneously questioning power relations at work.