α,β-Unsaturated amides are versatile building blocks in organic synthesis; however, forging C-C bonds at the γ-position is considerably more challenging than conventional β-addition. Herein, we report an iridium-catalyzed γ-hydro(hetero)arylation of α,β-unsaturated amides that delivers γ-adducts with high regioselectivity. Mechanistic experiments support an initial alkene isomerization to a β,γ-unsaturated intermediate, followed by γ-selective hydro(hetero)arylation. The coordinating amide functionality is essential for both reactivity and selectivity, enabling reactions with indoles and an electron-rich arene.