A probe insertion apparatus for real ear measurement includes a probe tube, a reference microphone, a reference speaker, an operator feedback device, a memory, and a processor. The processor is configured to direct the reference speaker to continuously emit reference sound, continuously receive reference signals from the reference microphone and tympanic reflection signals from the measurement microphone, and continuously make determinations of a tympanic distance between the sound receiving end of the probe tube and a tympanic membrane based on the reference and tympanic reflection signals and absent reference to a calibration measurement, as the operator moves the sound receiving end towards the tympanic membrane. The processor is also configured to automatically direct the operator feedback device to provide indicia of the tympanic distance between the sound receiving end of the probe tube and a tympanic membrane, as the operator moves the sound receiving end towards the tympanic membrane.