MSYS is a kind of "non-user-serviceable area" that you wouldn't deal with unless you were hacking on MinGW itself. Say you wanted to add some missing utility to MinGW, and there was some issue between MSYS and that utility requiring MSYS hacking.
If you think that you have a POSIX program that could benefit from being linked against MSYS, you're almost certainly better off just using Cygwin to port it. And now you can redistribute the Cygwin DLL with that program without tainting the program with the GPL.
https://support.microsoft.com/en-ca/kb/2977003
"Visual C++ Redistributable Packages install runtime components of Visual C++ Libraries on a computer that does not have Visual C++ installed. The libraries are required to run applications that are developed by using the corresponding version of Visual C++."
And an overview here:
https://msdn.microsoft.com/en-us/library/ms235299.aspx
Visual C++ libraries are not a core component of Windows; they are run-time support for Visual C++ programs. Microsoft calls them "redistributable".
If you write a program which depends on this, it behooves you to ship the exact version you're testing with and install it in the same directory as your executables. (See the "corresponding version" remark above from Microsoft themselves!)
(Which is why it is a myth that MinGW makes "native" Windows executables that don't need anything; in fact they rely on some program having been installed before them which rudely put some version of the MSVCRT.DLL into the System folder.)
Here's MSDN talking about it being a system component:
https://msdn.microsoft.com/en-us/library/abx4dbyh(v=vs.80).a...
At least since .NET 2003. It's handled differently in 2015.
https://blogs.msdn.microsoft.com/oldnewthing/20140411-00/?p=...
The trouble is (AIUI) that the GPL has an exception for system libraries, and MSVCRT.DLL is shipped with the system and MSVCRnnn.DLL are not. Microsoft legally allows you to redistribute MSVCRnnn.DLL, but does not provide source. Therefore, distributors of GPL apps linked against MSVCRnnn.DLL have no way to satisfy their legal obligations. So MinGW makes life easier for GPL apps, which are a significant part of the target audience, by linking against MSVCRT.DLL instead. This is worse from a software engineering point of view because you're using private / unstable API, but it is not illegal, and it lets you avoid the GPL issue.
The program that put MSVCRT.DLL in a system folder wasn't being rude; it was the Windows setup program itself, which was perfectly allowed to put it there. MinGW is being rude by looking for it. (However, if an app linked against one of the versioned libraries did not ship with the versioned library, then yes, it would be expecting some rude app to have copied the versioned library into the system folder.)
Now I'm even more motivated to stop using MinGW.
http://source.winehq.org/git/wine.git/tree/HEAD:/dlls/msvcrt
I don't know enough about MinGW to try it, but seems worth a shot!
If so, why did they actually create MSYS(2)? Why not just compile MinGW executables using gcc under Cygwin?
I have no idea. A cross toolchain for making Windows programs compiled with GCC, and linked with MSVCRT.DLL could be made available as a Cygwin package. All of the utilities for controlling the build can just be the Cygwin ones; all that is needed is the cross-gcc.