A system for evaluating a seal between an earphone of a hearing device and an ear canal that includes a first microphone positioned outside the ear canal, a second microphone positioned inside the ear canal, and a controller. The controller is configured to measure a sound level at one or more test frequencies using the first microphone, measure a sound level at the one or more frequencies using the second microphone, calculate a difference between the sound levels measured using the first and second microphones at each of the one or more test frequencies, and determine a measurement of an ear seal based on the calculated one or more differences.