Helical piles present a significant potential to create resilient, durable, and faster-to-construct foundations while ensuring a long-term and maintenance-free service life. To achieve their full potential, it is imperative that helical pile anchorages (i.e., pile-to-foundation connections) perform well without resulting in any cracking to the surrounding concrete. However, there is a lack of research and design guidelines on how to design resilient connections, especially for load conditions that create net uplift and cyclic loads. The objective of this study is to advance the current understanding and quantify the influences of anchorage bracket embedment depth, longitudinal reinforcement (ρx) percentage, shear span-to-depth (a/d) ratio, and the loading conditions on the load, deformation, cracking, and failure behavior of concrete foundations. For this purpose, 81 high-fidelity nonlinear finite element simulations of a pile cap strip are performed under monotonic tension, monotonic compression, and reversed-cyclic loads. The results indicate that the anchorage response may govern the response of the entire foundation system. Connection brackets with low embedment depths have been found to significantly reduce the load capacity of the foundation system, with a failure mode involving extensive anchorage zone cracking. The results also indicate that high ρx percentages and low a/d ratios should be used, along with higher embedment depths, in order to maximize the load resistance and prevent anchorage cracks for the load conditions involving tensile uplift loads. The research findings have applicability to both helical and micro piles given the fact that they both include similar anchorage conditions.