The enthesis is the attachment of ligament/tendon to bone and is one of nature’s solutions to the challenge of transferring load between dissimilar materials. Frequently injured and repaired, the healing enthesis fails to regain the properties that made it effective initially, highlighting the importance of understanding how it behaves mechanically. One of the essential barriers to date in doing so has been the visualization of the enthesis under load, a result stemming primarily from their small size. This project aims to overcome this obstacle through the use of specialized loading equipment, sample preparation and laser scanning microscopy. Further, finite element models were created to assess potential explanations for the observed behaviour. To our knowledge, this is the first time the enthesis has been simultaneously loaded and visualized at a level of detail corresponding to individual fibrils. Additional study may benefit from the established methodology and suggested mechanisms of load transfer.