Press hardening provides ultra-high strength steel components, typically boron steels, of complex geometries. In the process, the steel sheet is heated in a furnace to the austenitization temperature, transferred to the press, then simultaneously formed at high temperature and cooled in the die. Life limiting factors for the press hardening dies are mechanical fatigue, thermal fatigue, and wear. In the present case study two die segments were selected where critical damages were mechanical and thermal fatigue, respectively. The dies were made of a H13 type premium hot-work tool steel with complex heated die technology, die design integrating an advanced cooling system, for pressing automotive frame parts. The first die failed due to mechanical loading with a crack initiated from the ejector pin area. The die design, the mechanical loads, the elevated temperature, and the tool steel crack resistance are main factors to consider. In the second die cracks initiated from an ejector pin hole, as well, due to thermal cycles causing alternating compressive and tensile stresses at the surface, which led to crack nucleation because of the accumulation of local plastic strain in the surface.