Not many people complain of parachutes failing. It is usually too late. Like parachutes, inadequate insurance programs are many times discovered post haste following a catastrophe, often much to the surprise of management. In this book, we discuss some real-life stories of uninsured or underinsured disasters and coverage disputes. These stories are largely based upon our experiences as insurance expert witnesses in cases where an improperly designed insurance program led to years of litigation, unimaginable costs, and sometimes the bankrupting of the business and its owner. The mission of this book is to capture the attention of executives on why the way they may be buying business insurance could be all wrong and to provide suggestions on how to improve the process. We write this book as an antivirus scanning program of sorts for the insurance buyer to use in analyzing whether a business insurance agency and insurer are properly packing the company’s parachute.