An illustrative electroacoustic hearing system includes a loudspeaker and a processor configured to: direct the loudspeaker to present a sound to a recipient by way of a length of tubing extending from the loudspeaker to an ear tip disposed at an ear canal of the recipient, the directing configured to cause the sound to have a target sound pressure level at the ear canal; obtain a detected sound pressure level of the sound as the sound is presented at the ear canal, the detected sound pressure level obtained from a probe microphone disposed within the ear tip; identify a discrepancy between the detected and target sound pressure levels of the sound as the sound is presented at the ear canal; and direct, based on the identified discrepancy, a remedial action to be performed to compensate for the discrepancy.