ERP systems are now the digital backbone of today's businesses, enabling centralized control of business processes across departments. With the swift pace of digital transformation, the shift from legacy, conventional ERP to advanced technology such as Oracle ERP Cloud has taken the highest priority among organizations to foster agility, timely insights, and operational efficiency. This journal assesses the strategic imperative of Oracle ERP migration in overall digital transformation, with particular focus on best practices that ensure safe transition and effective system integration. The research puts forward a step-by-step ERP migration process with salient phases such as readiness assessment, data cleaning, stakeholder alignment, process reengineering, and phased deployment. The research analyzes Oracle's unique strengths scalable cloud architecture, embedded analytics, and AI-powered automation–and how they support digital goals such as improved user experience, compliance, and cost savings. The journal also identifies common integration challenges, which include legacy system compatibility, data migration complexity, resistance to change, and cross-functional coordination. The strategies in surmounting these threats are discussed in depth, some of which include embracing middleware solutions, effective change management frameworks, hybrid cloud strategies, and leveraging Oracle Integration Cloud in attaining seamless connectivity. This study contributes to the ERP modernization debate by presenting a realistic handbook for decision-makers, IT leaders, and enterprise architects orchestrating multi-year ERP overhauls. It reinforces that successful Oracle ERP migration involves more than just a technical makeover; it is a transformational process that must be aligned with strategic business objectives and future-ready digital capabilities.