This review summarizes advancements in Pd-catalyzed C(sp³)–H activation through various redox manifolds, including Pd(0)/Pd(II), Pd(II)/Pd(IV), and Pd(II)/Pd(0). While few examples of alkane C–H bond activation have been reported, numerous C(sp³)–H activation/C–C and C–heteroatom bond-forming reactions have been developed using directing group strategies to control regioselectivity and build structural patterns for synthetic chemistry. Effective mono- and bidentate ligands have also been identified to accelerate C(sp³)–H activation directed by weakly coordinating auxiliaries, enhancing reactivity and selectivity (including enantioselectivity) in Pd-catalyzed C–H functionalization reactions. The review highlights early developments in alkane C–H cleavage using stoichiometric Pd, which laid the foundation for recent catalytic processes. It also discusses the use of strongly coordinating auxiliaries to overcome the inert nature of C–H bonds, leading to the formation of various C(sp³)–C and C(sp³)–heteroatom bonds. Additionally, the review covers the challenges and solutions in Pd(II)/Pd(IV) and Pd(II)/Pd(0) catalysis, including the development of novel directing groups and the optimization of reaction conditions.This review summarizes advancements in Pd-catalyzed C(sp³)–H activation through various redox manifolds, including Pd(0)/Pd(II), Pd(II)/Pd(IV), and Pd(II)/Pd(0). While few examples of alkane C–H bond activation have been reported, numerous C(sp³)–H activation/C–C and C–heteroatom bond-forming reactions have been developed using directing group strategies to control regioselectivity and build structural patterns for synthetic chemistry. Effective mono- and bidentate ligands have also been identified to accelerate C(sp³)–H activation directed by weakly coordinating auxiliaries, enhancing reactivity and selectivity (including enantioselectivity) in Pd-catalyzed C–H functionalization reactions. The review highlights early developments in alkane C–H cleavage using stoichiometric Pd, which laid the foundation for recent catalytic processes. It also discusses the use of strongly coordinating auxiliaries to overcome the inert nature of C–H bonds, leading to the formation of various C(sp³)–C and C(sp³)–heteroatom bonds. Additionally, the review covers the challenges and solutions in Pd(II)/Pd(IV) and Pd(II)/Pd(0) catalysis, including the development of novel directing groups and the optimization of reaction conditions.