An increase in external shocks, international terrorism and natural disasters over the past two decades has led to unsustainable debt burdens in small and vulnerable states, resulting in debt restructuring programmes. This paper highlights the concerns of Commonwealth small states about their growing debt burden and the emerging challenges to their overall debt sustainability. It pinpoints the factors that lead to debt, the hurdles involved with debt restructuring and the weaknesses involved in debt management. It offers key lessons learned based on the experiences of seven small Commonwealth countries that have restructured their debts: Antigua and Barbuda, Belize, Dominica, Grenada, Jamaica, St Kitts and Nevis, and Seychelles.