This chapter aims to provide a critical overview of the World Bank’s loaning policies. Such a broad perspective would help better understand the conditions under which the Bank operates and the ways in which the borrowing countries could possibly benefit more from such loans. To even get a better sense, a preliminary distinction is made between the two key supranational banking agencies, namely the World Bank and the International Monetary Fund (IMF). Since both of these agencies have actively funded projects in many developing countries, drawing from their distinct borrowing and lending practices will be helpful in thinking critically about their outcomes. While acknowledging the World Bank’s track record in providing physical upgrading loans to assisting the low-income people, concepts including empowerment, enabling, and capacity building are also examined as considering physical upgrading as a panacea for these settlements would be naïve indeed. The chapter concludes that bridging the top-down physical upgrading approach and the bottom-up participatory component as the complementary attributes of any enabling effort.