A payment system may intelligently monitor text conversations on other applications or a user's email system. Users and participating merchants may enroll credit cards or other payment devices, bank accounts, etc., with the payment system. Once enrolled, a daemon/plugin of the payment system may monitor text applications, emails, or other communication means of the mobile computing device. Using Artificial Intelligence (AI) and Machine Learning algorithms, the payment system may determine payment information from a text or other communication, and initiate and/or complete a payment transaction between the communicating parties. Upon confirmation, the payment system may complete the funds transfer or payment to registered users or merchants in the text communication. The payment system may also integrate with a merchant's loyalty and reward programs and use these loyalty/reward points as forms of payment.