Examples are generally directed towards context-sensitive generation of conversational responses. Context-message-response n-tuples are extracted from at least one source of conversational data to generate a set of training context-message-response n-tuples. A response generation engine is trained on the set of training context-message-response n-tuples. The trained response generation engine automatically generates a context-sensitive response based on a user generated input message and conversational context data. A digital assistant utilizes the trained response generation engine to generate context-sensitive, natural language responses that are pertinent to user queries.