[lucajona]

Good question.

I think you'd want to pick Cygwin when you want to be able to compile and run POSIX apps on Windows without having to modify them too much.

However, if you just want a better command-line experience on Windows and want to easily install cross-platform open-source programs, I think Scoop is a better alternative to Cygwin.

If that is what you want, then not being a pain to use and setup is one good reason to pick Scoop :)

Also, Cygwin programs can only run under the Cygwin environment, whereas the programs Scoop installs are usually native programs that can be called from any other Windows program, or executed from a normal console. I assume there's a way to call Cygwin programs from a normal win program too--it's just more round-about.

[maxerickson]

Cygwin programs don't all depend on a Cygwin environment, most of the work occurs at the C library level. Some stuff might want a shell with more or different features than you get with the windows cmd shell.