In this work the relationship between the formal number of π‐electrons, d‐orbital conjugation topology, π‐electron delocalization and aromaticity in d‐block metallacycles is investigated in the context of recent findings concerning the correlation of π‐HOMO topology and the magnetic aromaticity indices in these species. It is demonstrated that for π‐electron rich d‐metallacycles the direct link between aromaticity, the number of π‐electrons and the frontier π‐orbital topology does not strictly hold and for such systems it is very difficult to unambiguously associate their aromaticity with the “4n+2” (Hückel) and “4n” (Möbius) rules. It is also shown that the recently proposed electron density of delocalized bonds (EDDB) method can successfully be used not only to quantify and visualize aromaticity in such difficult cases, but also – in contrast to magnetic aromaticity descriptors – to provide a great deal of information on the real role of d‐orbitals in metallacycles without the ambiguity of bookkeeping of electrons in the π‐subsystem of the molecular ring. Interestingly, some of the metallacycles studied cannot be classified exclusively as Hückel or Möbius because they have a hybrid Hückel‐Möbius or even quasi‐aromatic nature.