Inter-metropolitan mobility – the movements of people, products and goods in between cities and metropolitan areas – has uncharted potential in terms of sustainable and resilient development in low income climate-vulnerable countries commonly found in the Caribbean, sub-Saharan Africa, and South East Asia. However, transport development organizations that provide critical road infrastructure funding sources in these regions often hinder this potential because they lack consensus on how to prioritize investments and evaluate analytical and results’ outputs. Thus, their projects remain limited, unfocused and subsequently fail to improve sustainable and resilient development. This dissertation explores how development organizations make road infrastructure investments decisions. It focuses on 50 recent projects of the World Bank as that organization provides on average 22.1% to 36.8% of total transport investment from international public investments (WRI, 2014). It then delves deeply into a single case, Haiti, a top priority country that today has captured more than US$1.4 billion in road infrastructure transport funding since 2005 from the World Bank, the Inter-American Development Bank and the Government of Haiti. It proposes that international development entities can become more effective in achieving sustainable and resilient goals if they change some of their practices in inter-metropolitan mobility investments. To address this situation, this dissertation recommends that development banks improve their methodologies for prioritizing and aligning their investments, involve greater stakeholder engagement and engage in supporting capacity building.