Tremendous advances in transition metal‐catalyzed CH functionalization of the indole scaffolds have been recently reported. Great efforts have been devoted to the directing group strategy development in selectivity achievement overriding both the inherent reactivity of the indole scaffold and the activation of C2/C3H bonds. This article aims to highlight the elegant methods enabling the direct arylation, alkenylation, alkylation, and alkynylation along with the introduction of heteroatoms into indole scaffold via selective metal‐catalyzed CH activation strategies.