Clinical assessment of the human auditory system is an integral part of evaluating the health of a patient's cognitive processes. Conventional tests performed by audiologists include the Auditory Steady State Response (ASSR) and the Auditory Brainstem Response (ABR), both of which present an audio stimulus to the patient in order to elicit a change in brain state measurable by electroencephalography (EEG) techniques. Spatial monitoring of the electrophysiological activity in the auditory cortex, temporal cortex, and brain stem during auditory stimulus evaluation can be used to pinpoint to location of auditory dysfunction along the auditory pathway. However, given the obtrusive nature of conventional auditory evaluation techniques and the lack of information about sound transduction and cochlear dynamics usually irrecoverable by EEG, a better approach is needed to improve its clinical utility. Here, we present an in-ear device for auditory health assessment that integrates a sound engine for stimulation and high-density dry-electrode EEG for real-time simultaneous recording of brain activity. This system provides ease-of-use and patient comfort. We also investigate the auditory transfer function of the hearing system as an intricate convolution of the tympanic membrane, middle ear bones, and the cochlear subsystems.