In 2019 it was announced that the Isle of Wights iconic 1938 Stock tube trains were to be withdrawn and replaced with a new fleet of refurbished ex-London Underground trains, as part of a wider project to upgrade the Islands ageing railway infrastructure. This book examines in detail the events that followed: the infrastructure works, the withdrawal and disposal of the old trains, and the development and introduction of their replacements all of it carried out in the midst of a global pandemic. What went wrong, and what went right? What would happen to the 1938 Stock? And would the new trains even fit through Ryde Tunnel? In writing this book the author has been able to draw upon unique insights provided by some of the key figures involved in the Island Line upgrade, as well as by the current owners of many of the withdrawn 1938 Stock units.