High frequency ultrasound can enhance olive oil extractability industrially. However, the ultrasound attenuation phenomena and their implications on extractability, are not well understood. This work aims at evaluating the ultrasound attenuation effects on the oil extraction efficiency, while providing deeper insights into the physics behind the ultrasound extraction in a heterogeneous medium. Olives were collected and processed both in Italy and Uruguay during their respective harvest seasons. Sound pressure distribution was characterized in a high frequency ultrasound reactor, carrying 3 kg of water or paste, by using an indirect contact hydrophone device at 0.4 MHz or 2 MHz. A through-transmission ultrasonic technique was applied to determine attenuation profiles and coefficients in paste at the central frequency of each transducer, with various paste to water ratios and reactor sizes. Other ultrasound improvements on extractability were evaluated including reduction of malaxation time (10, 30 min), sonication time (2.5, 5 min) and power level (174, 280 W) without water addition and in a reactor with a 14.5 cm transducer to wall distance. However, no sound pressure levels in paste were detectable beyond 9 cm from the transducer at both frequencies. Among the various effects evaluated, an emission frequency of 0.4 MHz better improved extractability compared to 2 MHz. The attenuation profiles corroborated these findings with attenuation coefficients of 3.9 and 5.3 dB/cm measured near the respective frequencies. Improvements in oil extractability due to increasing sonication time and power level were significant (p < 0.05) also when sonicating beyond 14.5 cm and without water addition. Oil extractability improvements were observed even when sound pressure was undetectable beyond 9 cm from the transducer, suggesting that the standing wave oil trapping effect is not the governing mechanism for separation in high attenuation media for large scale systems.