Palladium‐catalyzed cross‐coupling and CH functionalization methods have long‐established selectivity and reactivity rules. Typically, these transformations afford a single new bond at a precise location on the substrate. Through the advancement of CH functionalization chemistry in the area of cooperative palladium/norbornene catalysis, novel selectivities and reactivities are possible. This cooperativity provides the opportunity to generate new bonds at remote or unreactive positions and afford multisubstituted products from simpler monofunctionalized starting materials. A robust understanding of these mechanistic steps is critical to understanding these reactions and utilizing their potential. Herein, we describe the mechanistic features and transformations of palladium/norbornene cooperative catalytic CH functionalizations.