This article dwells on the nature of “inverted bonds”, which refer to the σ interaction between two sp hybrids by their smaller lobes, and their presence in [1.1.1]propellane. Firstly, we study H3C−C models of C−C bonds with frozen H‐C‐C angles reproducing the constraints of various degrees of “inversion”. Secondly, the molecular orbital (MO) properties of [1.1.1]propellane and [1.1.1]bicyclopentane are analyzed with the help of orbital forces as a criterion of bonding/antibonding character and as a basis to evaluate bond energies. Triplet and cationic states of [1.1.1]propellane species are also considered to confirm the bonding/antibonding character of MOs in the parent molecule. These approaches show an essentially non‐bonding character of the σ central C−C interaction in propellane. Within the MO theory, this bonding is thus only due to π‐type MOs (also called “banana” MOs or “bridge” MOs) and its total energy is evaluated to approximately 50 kcal mol−1. In bicyclopentane, despite a strong σ‐type repulsion, a weak bonding (15–20 kcal mol−1) exists between both central C−C bonds, also due to π‐type interactions, though no bond is present in the Lewis structure. Overall, the so‐called “inverted” bond, as resulting from a σ overlap of the two sp hybrids by their smaller lobes, appears highly questionable.