Background: Supra-acetabular insufficiency fractures (SAIFs) occur in the upper acetabulum and are rare compared with insufficiency sacral, femoral head, or ischial fractures. However, SAIFs are known to occur in low grade trauma, and the underlying mechanism is still remained unclear. Methods: We performed biomechanical analysis using finite element analysis to clarify the mechanisms underlying the development of SAIFs. Patient-specific models and bone mineral density (BMD) were derived from pelvic computed tomography data from two patients with SAIF (unaffected side) and two healthy young adults. The bone was assumed to be an isotropic, linearly elastic body. We assigned Young's modulus of each element to the pelvis based on the BMD, and reported the relationships for BMD–modulus. Clinically relevant loading conditions—walking and climbing stairs—were applied to the models. We compared the region of failure risk in each acetabulum using a maximum principal strain criterion. Results: The average supra-acetabular BMD was less than that of the hemi-pelvis and femoral head, but was higher than that of the femoral neck and greater trochanter. Greater minimum principal strain was concentrated in the supra-acetabular portion in both the SAIF and healthy models. In the SAIF models, the higher region of the failure risk matched the fracture site on the acetabulum. Conclusions: Relative fragility causes compressive strain to concentrate in the upper acetabulum when walking and climbing stairs. When presented with a patient complaining of hip pain without apparent trauma or abnormal X-ray findings, physicians should consider the possibility of SAIF and perform magnetic resonance imaging for the diagnosis of SAIF.