The olive tree is an important crop in Portugal, where different levels of intensification coexist. The traditional olive orchards present profitability problems, mainly due to harvesting, so there has been a drastic reconversion towards high-density or super-high-density olive orchards. The latter present major constraints due to very specific needs for their use, being practically destined for new orchards. Consequently, the possibility of using systems based on canopy shakers in high-density olive orchards with local varieties is promising. The objective of this work is to evaluate a prototype canopy shaker for the harvesting of high-density olive orchards of the Portuguese variety ‘Cobrançosa’. The evaluation is based on the study of canopy shaking in order to adapt canopy training and the adaptability of the machine. For this purpose, the vibration of 72 points of the tree canopy was recorded and a qualitative assessment of the harvest was carried out. Differences were found between the different zones according to the direction of the forward movement of the harvester and the distance to the trunk. These differences were associated with the values obtained for fruit detachment, and a greater quantity of fruit was harvested in the areas of the canopy in contact with the rods.