According to the American Institute of Steel Construction (AISC) Specification for Structural Steel Buildings (AISC 360), the transverse plate-to-HSS bearing strength of rectangular hollow structural sections (HSS) under single-concentrated compression shall be determined based on the applicable limit states in Section J10. From all the limit states, both the web local yielding (WLY) and web local crippling (WLC) are applicable for transverse plate-to-HSS concentrated compression. However, all the limit state equations in J10 were originally developed for wide-flange sections. Unlike the in-plane compression on the web of a wide-flange section, the concentrated compression on an HSS member acts like an eccentric load on the HSS web and a distributed load along the HSS flange. The eccentric load on the web and flange local bending due to the distributed load can considerably reduce the failure load as compared to the wide-flange sections. Experimental and nonlinear finite element analyses (NLFEA) carried out in this study indicate that WLY, WLC, and flange bending always simultaneously occur at failure of an HSS; hence, they are not independent limit states. While AISC WLY equation predicts a strength closer to the experimental and NLFEA results, the bearing strength of HSS members can range from 16% to 66% of that predicted by AISC WLC equations. Based on actual failure modes, 251 FE models were analyzed, and a single transverse plate-to-HSS bearing strength equation under compression for HSS members was formulated.