A first input signal captured by one or more sensors associated with an ANR headphone is received. A frequency domain representation of the first input signal is computed for a set of discrete frequencies, based on which a set of parameters is generated for a digital filter disposed in an ANR signal flow path of the ANR headphone, the set of parameters being such that a loop gain of the ANR signal flow path substantially matches a target loop gain. Generating the set of parameters comprises: adjusting a response of the digital filter at frequencies (e.g., spanning between 200 Hz-5 kHz). A response of at least 3 second order sections of the digital filter is adjusted. A second input signal in the ANR signal flow path is processed using the generated set of parameters to generate an output signal for driving the electroacoustic transducer of the ANR headphone.