A New England insurance company had aging hardware, a database that was out of support, an older operating system, rising costs, and no disaster recovery plan. Craig Bogovich of NTT Data tackled this massive website backend, used by the company's insureds, providers, and partners, and architected a complete overhaul and ultimately deployed it into the cloud. Presented at Postgres Vision 2018, this presentation shows how the project unfolded and provided the strategies and methods used to modernize this legacy system with open source software and cloud technology.