The evolution of bookkeeping from manual ledger systems to intelligent accounting technologies represents a transformative shift in financial record-keeping. Traditional bookkeeping relied on handwritten entries, physical ledgers, and human calculations, which were not only time-consuming but also prone to errors, inefficiencies, and limited data accessibility. With globalization, business expansion, and increasing compliance demands, these methods have become insufficient. The transition began with computerized accounting software, automating basic financial processes and improving accuracy. Today, intelligent accounting systems powered by Artificial Intelligence (AI), Machine Learning (ML), cloud computing, and real-time analytics have redefined bookkeeping. These systems automate data entry, error detection, invoice processing, reconciliation, and report generation, drastically reducing manual intervention. They offer real-time financial insights, predictive analytics, and ensure higher compliance with regulatory frameworks. Intelligent systems also enable remote access, integration across ERP platforms, and scalability for businesses of all sizes. The shift enhances decision-making quality, strengthens internal controls, and aligns bookkeeping with strategic financial management. However, this digital transformation also introduces challenges such as cybersecurity risks, workforce reskilling needs, and technological dependence. Still, the ongoing evolution points toward a future where accounting becomes more advisory and analytical rather than transactional, marking a significant milestone in the modernization of financial practices.