The rapid advancement of Artificial Intelligence (AI) and Cloud Computing has opened new frontiers in retail automation. The Smart Trolley Billing System is an innovative solution designed to transform the conventional shopping experience by integrating AI-powered product recognition, RFID technology, and cloud-based billing into a single intelligent shopping trolley. This system enables automatic item detection, real-time billing, and seamless checkout without the need for traditional cashier counters. The system uses machine learning algorithms for product identification and a cloud platform to synchronize billing data in real time. This paper examines the architecture, functionality, challenges, and future scope of the Smart Trolley Billing System, highlighting its potential to reduce checkout queues, enhance customer satisfaction, and improve retail operational efficiency.