In this paper we undertake logical deep analyses of Ibn Sīnā’s (c. 980–1037) Flying (or Floating) Man based on Fazlur Rahman’s contribution to Muhammad Sharif’s A History of Islam Philosophy (1963). Next, we show how the Arabic original can contribute to an understanding of the thought experiment beyond the medieval Latin interpretation as after, for example, a recent publication by Dag Nikolaus Hasse. On the basis of the thought experiment analyses and comparison to contemporary postmodern thought experiments we conclude, among other things, that the traditional historical comparison between René Descartes’ Cogito and Ibn Sīnā’s Flying Man is rather unlikely.