While it basically works, PyPy's support for windows is not great: - The winconsoleio crashes and has been disabled (the winconsoleio-debug branch was last touched in July 2020), leaving PyPy with a suboptimal console experience. The unicode rendering does not work properly, so things like "rich" print out random ascii art. [0] - There is a problem with the posix interfaces. Things like os.listdir(dir-as-bytes) return slightly different results on CPython and on PyPy. This has made it difficult to support the missing `os.symlink` and `os.readlink`, which are becoming more popular as support for symlinks in windows improves. [1] - The only reason we still have unicode strings in RPython is to support windows (see  uses of space.realunicode_w). This makes even starting a RPython3 port much more difficult. It probably also slows down windows performance. - The work to create a windows installer was never finished (the windowsinstaller branch was last touched in Nov 2019) - There are builds of PyPy on windows at conda-forge, but they seem to be almost broken [2] How can we find contributors or sponsors to improve PyPy support for windows? Matti [0] issues 2999, 3767, 3768, [1] issues 3225, 2753, 3506, 3535, 3641, 3479, 3434 [2] https://github.com/conda-forge/pypy3.6-feedstock/issues/101