While ransomware is not a new cyber-threat, largely entering the cybersecurity scene in 2016 and 2017 with a number of high-profile attacks, research conducted by Enterprise Strategy Group reveals that a majority of organizations continued to experience ransomware attacks in 2019, representing a concern for both business and IT leadership teams. The research further reveals the prominence of cybersecurity insurance policies, and the relationship between ransomware payouts and those companies that hold these policies. A subset of organizations with cybersecurity insurance report that their providers are advising, and possibly even pressuring, them to pay cyber ransoms, further fueling the success rates and the economy built around ransomware. This disturbing trend sets the stage for the continuance of ransomware, and an opportunity for criminals to exploit those organizations that have engaged with cybersecurity insurance companies.