A payment chat bot can access a first chat text provided in a chat session by a merchant chat bot. The chat session is hosted by a chat service for communication between a plurality of chat application instances, where the payment and merchant chat bots simulate chat application instances. The method includes determining, based on the first chat text, whether to couple a payment session between a payment server and a merchant server for processing a payment transaction initiated from a chat application instance via the chat session. The method includes, in response to a determination to couple the payment session, coupling the payment session between the payment server and the merchant server.