A probe insertion apparatus for real ear measurement includes a probe tube, areferencemicrophone, a reference speaker, an operator feedback device, a memory, and aprocessor. The processor is configured to direct the reference speaker tocontinuouslyemit reference sound, continuously receive reference signals from thereferencemicrophone and tympanic reflection signals from the measurement microphone,andcontinuously make determinations of a tympanic distance between the soundreceiving endof the probe tube and a tympanic membrane based on the reference and tympanicreflection signals and absent reference to a calibration measurement, as theoperatormoves the sound receiving end towards the tympanic membrane. The processor isalsoconfigured to automatically direct the operator feedback device to provideindicia of thetympanic distance between the sound receiving end of the probe tube and atympanicmembrane, as the operator moves the sound receiving end towards the tympanicmembrane.