A processor is configured to perform headphone playback with a playback audio signal. The processor produces a feedback signal from an internal microphone, compresses the feedback signal according to a variable compressor setting, and determines a context of usage of the headphone, as being one of running or jogging, transportation, and critical listening. In response, the processor changes the variable compressor setting and drives the headphone speaker with the compressed feedback signal combined with the playback audio signal. Other aspects are also described and claimed.