This chapter explores the synergies, limitations, and challenges of addressing statelessness through human rights and development approaches, using the Hill Country Tamils of Sri Lanka as a case study. In addressing the legacy of statelessness, both the human rights and development frameworks must be drawn on and used simultaneously. However, a frameworks approach alone falls short in addressing statelessness, given the political, economic and societal factors that perpetuate discrimination. Instead, as the case of the Hill Country Tamils demonstrates, both human rights and development approaches must be underpinned by a deeper commitment to pursuing equality and combatting discrimination at large. Despite claims of success, the legacy of statelessness in Sri Lanka still lingers. The Hill Country Tamils are still among the ‘furthest behind’ in Sri Lanka and continue to experience severe discrimination well after securing formal citizenship. The community’s prolonged statelessness has led to long-term deterioration in human rights conditions, such that a grant of formal citizenship alone is inadequate to address structural drivers of disadvantage that the community continues to endure.