Expect runs things on a pseudo-terminal (pty) via IO::Pty. A pty is a Unix-ism for a fake serial termnial (tty) device that behaves (more or less) the way a serial console would. Windows console mode . . . stuff (for lack of a better term) doesn't work this way and hence there's no pty-y mechanism for Expect to use. You might see if the IPC::Run module's expect-like stuff works on Wintendo.