This book explores Jamaica’s contemporary relationship with the International Monetary Fund since 2010. It looks at Jamaica’s high debt and its inability to access financial support amidst international capital market restrictions, contextualizing harsh socio-economic realities. This book discusses Jamaica’s second return to the IMF and the resulting network of actors, governance and political and socio-economic efforts to re-engender a relationship with a “new’ IMF. Credibility was restored, demonstrated by and leading to the successful implementation of the 2013 Extended Fund Facility and subsequent exit to a Precautionary Stand-By Arrangement in 2016. Clarke and Nelson signal from their analyses lessons learned, discussing the economic prognosis for Jamaica as well as their relationship with the IMF under the shadow of the COVID pandemic.