Tl;dr if you have two files in a tar archive, one with an .exe extension and another without, but otherwise with the same name, e.g. test and test.exe, then both cygwin and msys2 tar will overwrite one of the files with the other on extraction. The developers insist that this is the correct behavior, refuse to even consider changing it and will barely even discuss it.

I've often run into cases like this where the developers insist on some ridiculous behavior and will not budge and even get angry if you question their decision. Another good example I found recently was with makepkg, a tool for creating packages for the pacman package system on ArchLinux. makepkg refuses to run as root. It used to have an option --asroot which would override this behavior but the devs decided to remove the option in recent versions. They insist that there is absolutely no reason that you would ever need to run makepkg as root and it is just too dangerous for you to be allowed to do so. This makes it extremely difficult to run makepkg inside a Docker container. They say you can just sudo to the nobody user but in Docker this takes many nontrivial steps.

Another good example is Bitcoin where the "core" devs currently have a strangle hold on the community. They've repeatedly made decisions that many disagree with. Now the community has split into warring factions yet still "core" retains its power.

Sure you can fork an Open-Source project but the power is held by those who control the most popular outlet for that software.