Railway transition zones (RTZs) are subjected to amplified degradation leading to high maintenance costs and reduced availability of tracks for operation. Over the years, several mitigation measures have been investigated to deal with the amplified degradation of these zones. However, to ensure the robustness of a design solution, it must be evaluated for critical conditions arising due to certain loading and track conditions. In this paper, the critical load conditions arising due to different velocities (sub-critical, critical and super-critical), the direction of the moving load, the combination of inertial effects and track imperfections (non-straight rail and hanging sleepers) and passage of multiple axles (using a comprehensive vehicle model) are investigated for an embankment-bridge transition. The results are then compared against the recently proposed design of a transition structure called SHIELD (Safe Hull Inspired Energy Limiting Design) to evaluate its performance under these critical conditions using various vehicle models and finite element models of the RTZs. It was found that the novel design of the transition structure effectively mitigates dynamic amplifications and results in smooth strain energy distribution across subcritical, critical, and super-critical velocity regimes in both directions of movement implying that the expected operation-induced degradation will be as uniform as possible in longitudinal direction. Furthermore, even though this transition structure is designed to deal with initial track conditions (perfectly straight track), its superior performance is not confined to tracks in perfect condition; it also efficiently addresses adverse effects from track imperfections such as hanging sleepers and non-straight rail. In the end, this work demonstrates the robustness of the design solution for all the critical conditions under study.