(1) Background: Pelvic fractures, and particularly instabilities of the dorsal pelvic ring, are becoming increasingly prevalent, particularly in orthogeriatric patients. Spino-pelvic triangular osteosynthesis is an effective approach to achieve sufficient stabilization in vertically unstable fractures. This study compares two types of osteosynthesis: the conventional one and a novel instrumentation where the iliosacral screw is placed through a fenestrated iliac screw. (2) Methods: Sixteen artificial osteoporotic L5+pelvis models with an unstable sacral fracture have been instrumented with either an iliac screw connected with a rod to a L5 pedicle screw and an iliosacral screw (TF) or a fenestrated ilium screw connected with a rod to a L5 pedicle screw and an iliosacral screw passing through the fenestra of the iliac screw (TFS). Biomechanical testing was performed using cyclic loading until failure. (3) Results: Both configurations yielded comparable results with regard to initial stiffness, implant loosening, and cycles to failure. The TFS exhibited markedly higher values for cycles to failure and markedly lower values for loosening. However, due to the characteristics of the artificial bone model, these findings were not significant. (4) Conclusions: The novel triangular fixation systems demonstrated comparable results to the standard triangular osteosynthesis configuration.