The Debt2Health Conversion Scheme of the Global Fund to Fight AIDS, Tuberculosis and Malaria is used to reassess a range of recent initiatives that propose debt relief in exchange for spending in the health sector. The experience with debt swaps in the mid 1990s was far from positive, and recent improved insight in the economics of debt relief suggests extreme caution. We argue that the recent spade of debt swap proposals, even if targeting countries and debt titles that fall outside current major international debt relief mechanisms, share most of the design faults of previous initiatives. Proposals such as Debt2Health do not constitute efficient vehicles to increase net transfers to poor countries, to reduce the economic disadvantages of indebtedness, or to strengthen public health systems of partner countries. For debt relief to constitute a valuable mechanism to provide aid, it should be designed as a large-scale and comprehensive operation, with spending earmarked to broad country-established priorities, and reinforce rather than undermine national implementation systems.