Scavenging energy from the earcanal’s dynamic motion during jaw movements may be a practical way to enhance the battery autonomy of hearing aids. The main challenge is optimizing the amount of energy extracted while working with soft human tissues and the earcanal’s restricted volume. This paper proposes a new energy harvester concept: a liquid-filled earplug which transfers energy outside the earcanal to a generator. The latter is composed of a hydraulic amplifier, two hydraulic cylinders that actuate a bistable resonator to raise the source frequency while driving an amplified piezoelectric transducer to generate electricity. The cycling of the resonator is achieved using two innovative flexible hydraulic valves based on the buckling of flexible tubes. A multiphysics-coupled model is established to determine the system operation requirements and to evaluate its theoretical performances. This model exhibits a theoretical energy conversion efficiency of 85%. The electromechanical performance of the resonator coupled to the piezoelectric transducer and the hydraulic behavior of the valves are experimentally investigated. The global model was updated using the experimental data to improve its predictability toward further optimization of the design. Moreover, the energy losses are identified to enhance the entire proposed design and improve the experimental energy conversion efficiency to 26%.