YS3 is a webzine for ZX Spectrum users that was started long ago (but not in a galaxy far, far away). In its earliest days it was updated on a roughly monthly schedule, which involved a group of people writing an awful lot of material in Word documents and Rich Text Files and sending them to me. I then converted all of these files into HTML by hand. It was as time-consuming as it sounds.

After a few months of this I realised that this was not a sustainable system, and began development of a simple Content Management System. It was not particularly user-friendly, lacking any kind of online document editing, but it was a vast improvement over the previous method. And as the years passed it grew gradually more fully-featured, eventually including both dynamic and static page generation, an AI-driven page layout feature and a simple forum used for team coordination.

The YS3 CMS was finally abandoned in favour of Wordpress in 2007.
The YS3 CMS was written entirely in Perl. What began as a simple RTF to HTML formatter gradually evolved into something more advanced, taking a set of RTF files and a simple config file to produce a complete and unique magazine-as-a-website, either dynamically or as a set of static pages. Soon it had its own mark-up language, so that the assorted writers could more easily add their own images or other non-text objects, and a little AI to place boxouts and images in appropriate places on the page.

Ultimately it was not a failure of the CMS that led to its being abandoned - the software itself was thoroughly tested and stable. However, organisationally the magazine format was no longer right for the site, and the blog-based CMS field was already thoroughly explored. The choice of Wordpress was the only logical one to make.