Compression members in steel bridges designed before 1960 may be deficient according to current design code requirements and so require strengthening. This paper explores the response of steel wide-flange columns reinforced with new steel flange cover plates, accounting for: residual and locked-in dead-load stresses; different yield strengths of the original W shape and the new cover plates; initial out-of-straightness; and load eccentricity at the member ends. A refined numerical analysis model is formulated and validated that computes the compressive resistance from principles of equilibrium, compatibility, and force–deformation relationships. Parametric studies conducted indicate that the capacity of the reinforced column is relatively insensitive to the magnitude of the locked-in dead-load stress in the original member, and that the strong axis capacity is insensitive to the magnitude of the residual stresses in the original member. A preliminary approach for designing strengthening for these members is presented and illustrated with an example calculation.