Content Management Systems (CMS) are software platforms designed to simplify the creation and management of websites and their content. Nowadays, about 50% of websites are powered by some sort of CMS platform. In this talk, we discuss our experience moving a complex CMS (i.e. WordPress) forward along the Progressive Web Road by integrating modern capabilities (e.g. Service Worker API) and progressive technologies (e.g. AMP) into its platform and ecosystem, and how the lessons learned can be applied to other CMSes.