This book explores the complex interplay between maritime insurance and piracy in the Indian Ocean, a crucial global trade route. Drawing on rich oral histories, this work delves into the lives of seafarers and insurance experts who confront the harsh realities of Somali piracy. Through a series of compelling case studies, including the notorious Maersk Alabama hijacking, the book sheds light on the evolving role of maritime insurers as they navigate the precarious waters of risk management. It highlights how these companies not only provide financial protection but also shape maritime security practices, transforming the sea into a managed space of governance. Spanning a geographical range from the Horn of Africa to global maritime hubs, the book emphasises the human cost of piracy and the often-overlooked experiences of those at sea. Bridging between historical cases and contemporary challenges, the book advocates a deeper understanding of the maritime landscape. Furthermore, by exploring the perspectives of seafarers, the book provides a unique insight into the emerging challenges faced at sea and the importance of safety in moments of maritime insecurity This book will be of much interest to students of maritime security, naval policy, the history of insurance, and international relations.