An exception (not a crash) is possible if a standard handle is invalid and a Popen call tries to replace one or two of the other standard handles (e.g. stdin is invalid and you pass the argument stdout=PIPE). Note that subprocess uses the standard handles directly, so this problem is unrelated to Python's sys.std* streams. IMO, the presence of an invalid handle in the standard handles should not cause Popen to fail. This is an old problem, and it should have been addressed a long time ago by substituting a handle for \\.\NUL.

In Windows 8+ this isn't particular to running pythonw.exe. In older versions such as Windows 7, if you start pythonw.exe from a console application, then the parent's standard handle values are copied to the pythonw.exe child. But these handles are invalid because pythonw.exe doesn't automatically attach to its parent's console. (You have to manually call AttachConsole(-1) or AllocConsole(), but that's complicated because you may need to reset the CRT's standard file descriptors and FILE streams and Pythons sys.std* streams.)

Note that pythonw.exe doesn't delete or close the standard streams. They're normally set to None because, in the default case, the Windows standard handles aren't valid in pythonw.exe, and thus the CRT maps its standard file descriptors (0, 1, and 2) to INVALID_HANDLE_VALUE (i.e. -1 cast as a pointer). For example:

    C:\Temp>pyw -2 -c "import msvcrt; open('test.txt', 'w').write(str(msvcrt.get_osfhandle(1)))"

    C:\Temp>type test.txt
    18446744073709551614

You can override this by starting pythonw.exe with explicit standard handles. For example, the following redirects stderr (2) to stdout (1) and redirects stdout to a pipe:

    C:\>set "script=import sys; print(sys.executable); print(sys.stdout); print(sys.stderr)"

    C:\>2>&1 pyw -2 -c "%script%" | more
    C:\Program Files\Python27\pythonw.exe
    <open file '<stdout>', mode 'w' at 0x00000000021FB0C0>
    <open file '<stderr>', mode 'w' at 0x00000000021FB150>

    C:\>2>&1 pyw -3 -c "%script%" | more
    C:\Program Files\Python36\pythonw.exe
    <_io.TextIOWrapper name='<stdout>' mode='w' encoding='cp1252'>
    <_io.TextIOWrapper name='<stderr>' mode='w' encoding='cp1252'>