<p>Elastomer–metal interfaces find applications in the automotive, aerospace, and biomedical industries, and are affected by environmental degradation, which is mainly corrosion, wear, and adhesion failure. Harsh service conditions, such as wet conditions, changes in temperatures, chemicals, mechanical forces contribute to the interfacial weakening process due to electrochemical reactions, crack propagation, and delamination, eventually cause a failure of the system. This review highlights the fundamental pathways of interfacial degradation and the interaction effect that occur between chemical, mechanical, and environmental stressors. An integrated system of chemo-mechanical–environmental degradation is considered, whereby corrosion, wear, loss of adhesion, and mechanical fatigue are not considered independent processes but rather they interact. This model emphasizes the acceleration of other stressors, which is caused by the damage of one stressor and by the feedback of other stressors at the elastomer–metal interface. The methods of mitigation are discussed, as well as surface treatment, incorporation of nanoparticles to strengthen the composite, the application of special adhesives, and bioinspired alternatives, such as sacrificial bonding and self-healing. Recent development of multifunctional elastomer–metal composites exhibit toughness and damping, corrosion resistance, and bond durability. Other issues highlight the importance of additional studies to solve the complexity of synergistic degradation in real-life scenarios. Smart coatings, predictive modeling, and resilient, sustainable, and adaptive materials are some of the future opportunities.</p>