Back when autocompletion and stuff were only available in Visual Studio/Xcode/Other bug IDEs, I was forced to use Ruby and fell in love with it. It didn't matter what I used as my editor was Sublime. But when VSCode came and language features became democratized, I never touched a type-less language again. Why should someone opt for a language with absolutely no features where one can have autocompletion, typecheckin…
These languages are really quite similar in many ways, but their domains ended up diverging. With python becoming the layman / scientific / learning language of choice, ruby has been pigeon holed into mostly web development.
Both are really easy to pick up and learn for somebody unfamiliar with CS concepts and I personally find the ruby syntax far more intuitive.
We have a lot more options now. For a while people tried to use python and ruby as glue / systems programming languages, but with golang and rust you have really good and more performant options in that space. And as you say the tooling has improved massively, so the hurdle of moving on to a more "rigid" language is less than it ever was.
I still really like ruby, and I think rails is still a powerhouse due to solving so many real world problems in a really complete package, but the lack of adoption outside of that niche has left it dwindling in popularity.