Protonation of benzocyclobutene under superacidic (HF-SbF5/SO2ClF) stable ion conditions was found to be a new independent route to Cram’s phenonium ion. On the basis of the observed C-13 NMR data, total chemical shift. difference (TCSD) criteria, ab initio theoretical and IGLO chemical shift calculations, and comparison with relevant models, the phenonium ion is indeed a spirocyclopropylbenzenium ion (spiro[5.2]octa-5,7-diene-4-yl cation) with a 4 pi cyclohexadienyl system and additional cyclopropylcarbinyl delocalization. It can not be characterized as a nonclassical Freudenberg type ion which should contain a hypercoordinate sp(2) carbon and display 6 pi aromatic nature. In an attempt to prepare a de facto nonclassical phenonium ion 2-fluoro(tetrafluoro)benzonorbornene, containing a strongly deactivated aromatic ring, was ionized under long lived stable ion conditions, but it gave instead the corresponding tetrafluorobenzonortricyclyl cation. On the basis of the observed C-13 NMR data, TCSD, and comparison with its parent analog this ion too is of predominantly spirocyclopropylbenzenium ion nature.