The paper recalls some skeptical comments Norbert Wiener made regarding the potential use of cybernetics in social sciences. A few social scientists were seduced by cybernetics from the beginning, but cybernetics never really caught on in sociology. The paper argues that one reason for this may lie in the mathematical theory of communication entertained by early cybernetics. This theory which maintains that there are probability distributions of possible communication is at odds with the sociological theory’s idea of a communication driven by improbable understanding. Yet the move from first-order cybernetics to second-order cybernetics, by re-entering the observer into the very systems she observes, provides for a bridge between cybernetics and sociology.