<p>In this study, we develop and investigate an analytical model of a bistable damped oscillator coupled with a linear resonator, supported by numerical simulations and experimental validation. Bistability is realised through slender beams buckled under axial compression, forming the core of the system. The proposed analytical and numerical tools can capture the key nonlinear dynamics of the coupled system. The response of the bistable oscillator–linear resonator system under external excitation is initially analysed and compared with that of a stand-alone oscillator. By varying excitation amplitude and frequency, a rich spectrum of nonlinear behaviours is revealed—from intrawell oscillations to interwell transitions and bifurcations—and is thoroughly characterised. The integration of a linear resonator is shown to enhance vibration attenuation across multiple frequency bands and improve the predictability of chaotic regimes. Experimental validation is then conducted using additively manufactured pre-buckled bistable beams and linear resonators. Nonlinear system identification confirms the influence of friction and complex damping, aligning well with predictions. Tests which compare oscillators with linear and bistable beams coupled to resonators demonstrate the effectiveness of pre-buckled beams in producing bistable springs. Finally, simulation accuracy is shown to degrade significantly close to chaotic response regimes, emphasising the sensitivity of bistable systems to parameter variations, test conditions, and manufacturing tolerances.</p>