Abstract Meniscus efficacy at promoting joint congruity and preventing osteoarthritis hinges on enthesis integrity. Gross-scale tensile testing, histomorphometry and magnetic resonance imaging reveal significant differences between the four attachments, implying that each must endure a unique mechanical environment, which dictates their structure. However, little data exists to elucidate how these interfaces have adapted to their complex loading environment, particularly on a relevant scale, as the enthesis transitions through several unique zones in less than a millimeter. In our study we leveraged nanoindentation to determine viscoelastic material properties through the transition zones. Additionally, we employed histological techniques to evaluate the enthesis structure, including collagen organization and interdigitation morphometry. Mechanical evaluation revealed the medial posterior insertion site to be significantly more compliant than others. Collagen fiber orientation and dispersion as well as interdigitation morphometry were significantly different between attachments sites. These findings are clinically relevant as a disproportionate amount of enthesis failure occurs in the medial posterior attachment. Also, meniscal enthesis structure and function will need to be considered in future reparative and replacement strategies in order to recreate native meniscus mechanics and prevent osteoarthritis propagation.