In org-mode, pressing M-S-RET (meta-shift-return) will create a new TODO on a new line. This key sequence sends M-RET to
In general, lots of keystrokes are simply impossible to send via a terminal, since terminals emulate an old protocol that only allowed 256 separate keys (or maybe only 128).
Chances are, when you press S-RET, Terminal.app does exactly the same thing as if you'd pressed RET. Thus Emacs has no way to distinguish those two cases.