It is becoming more and more obvious that the software risks and complexity that face today’s legacy systems is a growing problem for many IT organizations. Are these legacy applications “Ever going to be replaced or retired? Are they “Too Big to Fail”? Added concern around many of these applications involves their size and architectural interconnectivity whereby their failure would prove disastrous to the entire business. There are few industries where this is more evident than the insurance industry. At our recent IT Executive Dinner with stakeholders from the Insurance industry, conversations were centered around application modernization, legacy application rationalization, and the funding mechanisms Insurance IT organizations use to improve their application assets.