Intelligent agents (IA) for automatically generating responses to content within a communication session (CS) are disclosed. An IA is trained to target the responses to a user and the user's context within the CS. An IA receives CS content that includes natural language expressions encoding users' conversations and determines content features based on natural language models. The content features indicate intended semantics of the expressions. The IA identifies likely-relevant content to the targeted user, to generate a response for. Identifying such content includes determining a relevance of the content based on content features, a context of the CS, a user-interest model, and a content-relevance model. Identifying the likely-relevant content to respond to is based on the determined relevance of the content and relevance thresholds. Various responses to the identified portions of the content are automatically generated and provided based on a natural language response-generation model targeted to the user.