Strengthening applications form a significant field of research, which is reflected in significant relevant publications and dedicated scientific conferences, while practice-oriented guidance documents and standards have been published in the recent years and they substantially support the implementation of strengthening methods. At the same time, this very implementation strongly relies on the connection of new to existing components in order to achieve the desired strengthening outcome in stiffness, deformability, or load-bearing capacity. This transfer mechanism may often be realized through mechanical anchorage by use of postinstalled anchors. Such anchors are generally expected to efficiently transfer seismic actions between steel and concrete, or within concrete interfaces. Moreover, many seismic retrofitting techniques would not be realizable without the use of post-installed anchors. This paper focuses on the structural performance of such connections in a challenging retrofitting method, namely a diagonal bracing with structural steel profiles, and by the use of high-performance undercut anchors. The investigation considers a concrete frame found in existing structures and it delivers insights on the structure's performance before and after the strengthening application, based on a set of advanced, non-linear finite element model analyses.