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This study examines the role of digital technologies in enhancing supply chain flexibility and responsiveness in dynamic and uncertain operational environments. The growing complexity of global supply networks, coupled with market volatility, evolving customer expectations, and technological disruption, has driven organizations to adopt advanced digital tools to maintain competitive advantage. Employing a qualitative research design, data were collected through semi-structured interviews with twenty-five supply chain managers, IT specialists, and operations leaders across manufacturing, logistics, and retail sectors. Thematic analysis revealed how organizations leveraged technologies such as artificial intelligence, the Internet of Things, blockchain, digital twins, and cloud-based platforms to anticipate disruptions, optimize operations, and enable rapid decision-making. AI supported predictive and prescriptive decision-making for demand forecasting, scheduling, and resource allocation; IoT provided real-time operational visibility for timely responses; blockchain ensured transparency and trust across multi-tier networks; digital twins enabled virtual simulation and scenario testing; and cloud platforms improved collaboration across dispersed teams. The study also highlighted critical human and organizational enablers, including leadership support, digital literacy, cultural readiness, and cross-functional collaboration. Integration of sustainability objectives demonstrated that operational efficiency, adaptability, and environmental responsibility could coexist. Overall, the findings emphasize the interplay between technology, organizational capabilities, and inter-organizational collaboration in achieving agile, resilient, and sustainable supply chains, offering valuable insights for both theory and practice.