This document discusses the history of the oldest Django project, which was originally created for a regional news company with newspapers, TV stations, and magazines. It details the challenges of porting the project to newer versions of Django over many years as Django continued to evolve, including two major porting attempts. Key lessons learned include the importance of preparation, testing, and making deployment automated. The project was later open sourced and the codebase simplified, cutting around 40,000 lines of code.