AbstractThe interface between two‐dimensional (2D) materials and soft, stretchable polymeric substrates is a governing criterion in proposed 2D materials‐based flexible devices. This interface is dominated by weak van der Waals forces and there is a large mismatch in elastic constants between the contact materials. Under dynamic loading, slippage, and decoupling of the 2D material is observed, which then leads to extensive damage propagation in the 2D lattice. Herein, graphene is functionalized through mild and controlled defect engineering for a fivefold increase in adhesion at the graphene‐polymer interface. Adhesion is characterized experimentally using buckling‐based metrology, while molecular dynamics simulations reveal the role of individual defects in the context of adhesion. Under in situ cyclic loading, the increased adhesion inhibits damage initiation and interfacial fatigue propagation within graphene. This work offers insight into achieving dynamically reliable and robust 2D material‐polymer contacts, which can facilitate the development of 2D materials‐based flexible devices.