Sri Lanka, the teardrop-shaped island in the Indian Ocean, is facing its worst political–economic crisis since independence. This book is a compilation of essays on several themes which trace the nation’s recent journey, from the rise of the Rajapaksa regime in 2019 to the present crisis in 2022. The essays explain how the nation moved from a democratic country to a full-scale autocratic, militarized nation. The US–India–China triangulation and its impact on Sri Lanka are also captured in this book, bringing a unique Sri Lankan perspective. Teardrop Diplomacy will give the reader a better understanding of the underlying political and social distress in everyday life in Sri Lanka and what brought the fragile state to this political and economic disaster within a short period of three years. This is a lesson for many developing nations, especially those under debt-distress in the post-pandemic environment.