Extended single-plate shear connections can be subjected to compression loads in addition to shear loads during extreme events like wind and earthquakes. However, the existing interaction equations found in the AISC Steel Construction Manual, in literature, and in design examples—which are being used in design for combined loading cases—have not been formally validated for use by experimental testing or finite element analysis. This research aims to study the behavior of these connections when subjected to combined loading of shear and compression force by performing a nonlinear finite element analysis in ABAQUS. The variables considered in the study are column web stiffness, connection configurations, and different bracing conditions of the beam. The results from these analyses were compared to the available interaction equations in the AISC Manual and in literature to assess their applicability under different conditions. Shear-compression interaction plots were generated from the results that show the shear strength decreases with an increase in compression force in the connection. The effect of the compression force on the shear strength depends on the column web’s rigidity and the bracing condition of the beam.