A system is configured to replay a selected conversation with a selected agent. The selected conversation may be selected from a plurality of previously conducted conversations with other agents. The selected agent may be selected from a plurality of available agents. The system determines various tasks, named entities, and user preferences from the selected conversation. During a replay of the selected conversation with the selected agent, the system generates responses to messages received from the selected agent based on the determined tasks, named entities, and user preferences. The system also allows a user to select whether the replayed conversation should be conducted in a passive mode or in an active mode. In a passive mode, the system generally conducts the replayed conversation autonomously whereas, in an active mode, the system requests user input before sending a response to the selected agent.