An electronic audio device for use with at least one earpiece or a pair of earpieces, or a pair of earpieces in a headphone, each earpiece having a microphone and a speaker located therein, including circuitry operatively coupled to the microphone and speaker, and a processor operatively coupled to evaluate a seal quality of the earpiece to a user's ear based on seal quality measurements made while driving or exciting a signal into the speaker located in the earpiece and where the processor is configure to generate a visual or audio message identifying whether at least one earpiece is properly sealed based on the seal quality measurements.