This video was originally recorded in March 2011. Hey Honey, the server’s down again! That’s the phrase I hear all too often, because our home-grown ZENPRESS CMS (which I’ve been building since 1997) lives on top of an older engine that simply can’t handle a 13 years worth of data. Last year, I decided to move to a more future-proof system. Because ZENPRESS has 53238 articles encoded with our own custom editorial markup language and a boatload of custom features, I’ve been writing a Web framework and a series of plug-ins that move our custom ZENPRESS CMS feature stack into WordPress. This presentation is the story of the first programming year of that migration, why I chose WordPress, some of the design principles that were set out, tricks and lessons I’ve learned, a tour of some of the cool plug-ins I’ve developed so far, and tips and hints for anyone else who might want to try migrating a large, custom system while still retaining some shred of sanity. Special thanks to Mason James at WPMU Dev for filming this video.