Most likely, as Adam directly "credited" their revenue issues to AI (which makes sense, tailwind was making money by selling pre-made components, but now the AI can generate those for you).
The test for writing a book is whether the author applied their own judgement in the creation of the book. Even if some explanations of concepts are inevitably similar the structure of the book, the example code, etc. will reflect the author's judgement and experience.
An LLM is incapable of authorial intent. It's not synthesizing the docs with a career of experience and the input of an editor. It's playing madlibs with the work of one or more prior authors.
All customers already had lifetime access and couldn't pay more. Plus noone was reading the docs on the webpage anymore.
Recurring subscriptions, ads in AI products (think Tailwind MCP server telling you about subscription features.) Those were just two things I pulled out of the hat in a minute.
I've experienced this in my own life - I ran my own business and I had to choose between doing a worse job and enshittifying the product to make more money, or doing a good job but risking bankruptcy. I choose bankruptcy, because I believed strongly in doing a good job and not enshittifying the product. I don't regret it.
Well you always could just read the docs instead of using the paid offer. Took longer. Not anymore.
Now? Well, AI solves the entire issue of time taken typing. Classnames always looked cleaner too. Additionally CSS doesn't lag behind Browser features and comes with the full power of the language.
Why bother with Tailwind anymore whatsoever?
They were extremely lucky that AI picked up tailwind to keep it relevant, they should be keeping up with the times if they want to stay relevant. Instead their actions are those of someone that is cowering in fear, making sure that they can put the last of the revenue into the coffer. (reject PR because they don't want AI to do better with tailwind while firing engineers, not to mention the big tantrum).
Lets go back to actual CSS, it is easier to read anyway, it's now a modern tool with variables and all that, there's no longer a need to dumb it down.
Besides, if I wanted to pay for pre-made components, I would go with DaisyUI which is agnostic to the frontend framework, unlike the paid components from tailwindLabs, which strictly require you use one of the javascript frameworks.