Hot work tool steels (HWS) are widely used for high performance components as dies and molds in hot forging processes, where extreme process-related mechanical and thermal loads limit tool life. With the functionalizing and modification of tool surfaces with tailored surfaces, a promising approach is given to provide material flow control resulting in the efficient die filling of cavities while reducing the process forces. In terms of fatigue properties, the influence of surface modifications on surface integrity is insufficiently studied. Therefore, the potential of the machining processes of high-feed milling, micromilling and grinding with regard to the implications on the fatigue strength of components made of HWS (AISI H11) hardened to 50 ± 1 HRC was investigated. For this purpose, the machined surfaces were characterized in terms of surface topography and residual stress state to determine the surface integrity. In order to analyze the resulting fatigue behavior as a result of the machining processes, a rotating bending test was performed. The fracture surfaces were investigated using fractographic analysis to define the initiation area and to identify the source of failure. The investigations showed a significant influence of the machining-induced surface integrity and, in particular, the induced residual stress state on the fatigue properties of components made of HWS.