South Asian regionalism, envisaged as a framework for cooperative development and collective security, has faced persistent challenges since the inception of the South Asian Association for Regional Cooperation (SAARC) in 1985. The dominant narrative of Indian–Pakistani rivalry, structural asymmetries among member states, and the inability of SAARC to evolve into an effective multilateral institution have stymied regional integration and cooperation. In response, India has progressively reoriented its regional engagement toward alternative frameworks such as the Bay of Bengal Initiative for Multi-Sectoral Technical and Economic Cooperation (BIMSTEC), aligning with its broader foreign policy goals including the ―Act East‖ and ―Neighbourhood First‖ initiatives. This paper examines India’s historical role and evolving strategies in South Asian regionalism, critically analysing the limitations of SAARC, the emergent collaborative prospects through sub-regional mechanisms, and India’s potential to reshape regional cooperation beyond the shadows of rivalry. By exploring political, economic, and security dimensions of regionalism, it highlights how India can transition from a posture defined by bilateral tensions to one that fosters inclusive cooperation, connectivity, and shared prosperity across South Asia. The study suggests that genuine regional collaboration will depend on structural reform of existing institutions, multifaceted cooperation in trade and infrastructure, and India’s diplomatic willingness to reconcile strategic interests with collective regional goals.