However, the precise mechanism underlying its highly robust catalytic activity has remained a subject of debate, leading to active discussions and various explanations proposed over the past decades. Considering this, the unexpectedly efficient mechanism discovered for the π-type activated Michael addition catalysed by I 2 has been meticulously characterised and elaborated. This analysis aimed to gain mechanistic insights into the complex nature of the interaction between I 2 and the α-carbon of the π-type activated trans-crotonophenone substrate. The investigation encompasses an extensive exploration of various structural attributes, including bond lengths, hybridisation angles, and characterisation of the interaction using QTAIM methods and descriptors, including ρ BCP , Laplacian (∇ 2 ρ(r)), and H value.