Cygwin is terrible but there are alternatives, such as:

https://github.com/bmatzelle/gow

Which work extremely well. I can go back and forth between Debian and windows without too much trouble. Many tools are cross platform.

How is Cygwin terrible exactly? It’s fast and lightweight (compared to other recommendations like MobaXterm) and has a huge selection of packages¹. Frankly, I don’t get why Cygwin gets so much flack; I’m glad it exists.

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¹ — http://cygwinports.org/

Also msys2 which is well maintained.

And then there's vagrant. I switched back to MS because C# and profit, all other dev is on vagrant boxes which actually made things easier as I tend to be more comfortable with that what I push will work as I have the same *nix setup on my 127.0.01 as on remote.

True, I had not thought of that. Any shortcomings?

Vagrant under VirtualBox is a little slow, but taking the time to set up WinNFSd is very worthwhile for real file I/O gains. If you want to pay for VMWare + VMWare's Vagrant plugin, you'll get even better performance.

Supposedly you can also use Hyper-V which is included by default on Windows 8 and later. But since the time I found that I didn't yet have a need for vagrant again.

I'm currently on Win10 Home, but I use Vagrant so extensively that it's probably worth an upgrade (besides that, it provides a lot of other great features, anyway).