This technology includes systems and methods which allow for a determination of the attenuation and fit of a hearing protection device based on images of a user’s ear. This technology can be used in a wide range of industrial and military settings including but not limited to factories, construction sites, mines, mills, airports, railroads, and military combat training environments. A photograph of a person’s ears wearing hearing protection devices can be used to estimate whether or not that person is achieving sufficient or adequate attenuation to protect their ears against harmful noise exposure. Earplug manufacturers could provide the test attenuation data from their laboratory tests along with paired photographs of the subjects and the fitting estimation algorithm can be trained for new products.