The efficacy of retainers is a pivotal concern in orthodontic care. This study examined the biomechanical behaviour of retainers, particularly the influence of retainer stiffness and tooth resilience on force transmission and stress distribution. To do this, a finite element model was created of the lower jaw from the left to the right canine with a retainer attached on the oral side. Three levels of tooth resilience and variable retainer bending stiffness (influenced by retainer type, retainer diameter, and retainer material) were simulated. Applying axial or oblique (45° tilt) loads on a central incisor, the force transmission increased from 2% to 65% with increasing tooth resilience and retainer stiffness. Additionally, a smaller retainer diameter reduced the uniformity of the stress distribution in the bonding interfaces, causing concentrated stress peaks within a small field of the bonding area. An increase in retainer stiffness and in tooth resilience as well as a more oblique load direction all lead to higher overall stress in the adhesive bonding area associated with a higher risk of retainer bonding failure. Therefore, it might be recommended to avoid the use of retainers that are excessively stiff, especially in cases with high tooth resilience.