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Testing getpass shouldn't be that difficult if you use ctypes to call WriteConsoleInput [1]. For example:
 from ctypes import *
 from ctypes.wintypes import *
 kernel32 = WinDLL('kernel32')
 IN, OUT, INOUT = 1, 2, 3
 KEY_EVENT = 0x0001
 STD_INPUT_HANDLE = -10
 STD_OUTPUT_HANDLE = -11
 STD_ERROR_HANDLE = -12
 INVALID_HANDLE_VALUE = HANDLE(-1).value
 class KEY_EVENT_RECORD(Structure):
 class UCHAR(Union):
 _fields_ = (('UnicodeChar', WCHAR),
 ('AsciiChar', CHAR))
 _fields_ = (('bKeyDown', BOOL),
 ('wRepeatCount', WORD),
 ('wVirtualKeyCode', WORD),
 ('wVirtualScanCode', WORD),
 ('uChar', UCHAR),
 ('dwControlKeyState', DWORD))
 class INPUT_RECORD(Structure):
 class EVENT(Union):
 _fields_ = (('KeyEvent', KEY_EVENT_RECORD),)
 _fields_ = (('EventType', WORD),
 ('Event', EVENT))
 PINPUT_RECORD = POINTER(INPUT_RECORD)
 class HANDLE_IHV(HANDLE):
 @classmethod
 def _check_retval_(cls, retval):
 if retval.value == INVALID_HANDLE_VALUE:
 raise WinError(get_last_error())
 return retval.value
 def errcheck_bool(result, func, args):
 if not result:
 raise WinError(get_last_error())
 return args
 def WINAPI(name, dll, restype, *argspec):
 if argspec:
 argtypes = tuple(p[0] for p in argspec)
 paramflags = tuple(p[1:] for p in argspec)
 else:
 argtypes = paramflags = ()
 prototype = WINFUNCTYPE(restype, *argtypes, use_last_error=True)
 func = prototype((name, dll), paramflags)
 if restype in (BOOL, HANDLE):
 func.errcheck = errcheck_bool
 setattr(dll, name, func)
 WINAPI('GetStdHandle', kernel32, HANDLE_IHV,
 (DWORD, IN, 'nStdHandle'))
 WINAPI('WriteConsoleInputW', kernel32, BOOL,
 (HANDLE, IN, 'hConsoleInput'),
 (PINPUT_RECORD, IN, 'lpBuffer'),
 (DWORD, IN, 'nLength'),
 (LPDWORD, OUT, 'lpNumberOfEventsWritten'))
 def write_console_input(s):
 hInput = kernel32.GetStdHandle(STD_INPUT_HANDLE)
 recs = (INPUT_RECORD * len(s))()
 for c, rec in zip(s, recs):
 rec.EventType = KEY_EVENT
 rec.Event.KeyEvent.bKeyDown = True
 rec.Event.KeyEvent.wRepeatCount = 1
 rec.Event.KeyEvent.uChar.UnicodeChar = c
 return kernel32.WriteConsoleInputW(hInput, recs, len(recs))
 if __name__ == '__main__':
 import getpass
 test_input = 'Console test input.\n'
 n = write_console_input(test_input)
 assert n == len(test_input)
 read_input = getpass.getpass()
 assert read_input == test_input.rstrip()
This requires that python.exe is run with an attached console (conhost.exe), i.e. the process can't be created as a DETACHED_PROCESS [2] nor can it be run using pythonw.exe without first calling AllocConsole.
 
[1]: https://msdn.microsoft.com/en-us/library/ms687403
[2]: https://msdn.microsoft.com/en-us/library/ms684863