This study investigates how Generative AI (GenAI) chatbots mediate sensemaking in organizations, particularly in contexts characterized by equivocality. Drawing on the enactment model by Weick and colleagues (2005), we analyze how GenAI technology interacts with workers during sensemaking. Our findings reveal that GenAI chatbots act as assistants, collaborators, and facilitators, by both introducing as well as reducing equivocality in an organizational context through iterative dialogue and contextual adaptation. The chatbots do not only transform cues into actionable insights, they also introduce novel ways of structuring and interpreting information. Furthermore, workers’ presumption of the chatbot behavior shapes their interaction with it, influencing its role in navigating equivocality during sensemaking. By extending theoretical boundaries of technology-mediated sensemaking, this research provides actionable insights into leveraging GenAI for organizational resilience and adaptability in dynamic environments.