alt Hacker NewsCygwin was fun. I'd done zero development on Windows, but about 10 years ago I had to figure out how to deploy some nightly shell scripts across a bunch of local computers in a few dozen offices, where about 80% were MacOS and the rest were Windows. I don't remember exactly how I rigged it, but basically cygwin allowed me to keep the scripts as they were and trigger them in place, with a few small modifications.
I never want to deal with that again ;)
[edit] fwiw, Termux on Android is similarly a fun pseudo-environment. It's a nice and helpful toy.
The biggest issue I remember is directory seperators... windows of course using \ which bash would then interpret as an escape. Cygwin mostly papered over that from what I can recall, but it could lead to some weirdness, like sometimes you'd get C:\\path\\es\\like\\this