The design of end-plate connections for steel structures is more loosely specified in Chilean regulations than in American regulations. Nevertheless, eight-bolt extended stiffened (8ES) end-plate connections have not derived benefit from extensive past research, and therefore, their normative recommendations are quite constraining. In this study, both the prequalification and qualification limits are evaluated, and the linear and nonlinear analyses of a connection from a case study focused on a typical industrial structure, characterized by its reduced dimensions, are carried out. For the design of the connection, a spreadsheet was developed based on AISC 358. The nonlinear analysis was modeled using the finite element method, and it is confirmed that the normative recommendations restrict the design in a very conservative way, resulting in oversizing. Finally, a new optimized connection configuration is proposed and analyzed without stiffeners.