Friction control at the wheel–rail interface, using on-board solid stick friction modifier systems can lead to enhanced track life, reduced wear, and increased fuel economy in railroads. Frictional contact between the solid stick and the railway wheel itself can potentially cause vibrations within the modifier systems, influencing their stability and performance. A frequency domain linearized stability analysis of the state of steady sliding at the frictional contact between the solid stick and the wheel is performed. The proposed approach relies on individual frequency response functions (FRFs) of the wheel and the applicator–bracket subsystems of the on-board friction modifier. Stability characteristics of three representative bracket designs are qualitatively compared, using the FRFs generated by their respective finite element (FE) models. The FE models are validated by comparing the predicted natural frequencies with corresponding experimentally measured values on a full wheel test rig (FWTR) facility. The validated FE models are then used to compute stability maps which delineate stable and unstable regions of operation in the design parameter space, defined by train speed, angle of applicator, friction coefficient, and bracket design. Strong dependence of stability upon the bracket designs is observed. The methodology developed here can be used by design engineers to assess the effectiveness of design changes on the stability of the applicator–bracket assembly in a virtual environment—thus avoiding costly retrofitting and prototyping. Directions for further model refinement and testing are provided.