The α-activation of ketones represents a cornerstone in modern organic synthesis, unlocking many pathways for constructing complex molecular architectures. In conventional systems, the reactivity at the α position of ketones is well-documented, but it can be further modulated by placing these molecules in constrained environments such as those provided by carbaporphyrin scaffolds. However, despite the potential advantages and the extensive research into cobalt catalysis, no known cobalt-assisted transformation currently leads to the arylation of an α-carbon atom in simple ketones, like acetone. The structural rigidity and electronic properties of carbaporphyrins can impose unique steric and electronic effects on the coordination sphere of the encapsulated metal centre, potentially altering the typical reactivity patterns (or lack of such) observed for both the metal and the bound substrate, including keto-enol equilibrium in the case of the activated ketones. In this context, our research seeks to address this gap by systematically investigating the reactivity of a series of ketones confined within cobalt carbaporphyrin complexes. Through these studies, we aim to elucidate the mechanistic aspects of this confinement and its impact on the cobalt-assisted αactivation and subsequent arylation of ketones with a carbaporphyrin fragment (azulene or pyrrole moiety), as well as the attached fragment behaviour towards the confining framework.