One of the major advantages of micromachining is the high achievable surface quality at highly flexible capabilities in terms of the machining of workpieces with complex geometric properties. Unfortunately, finishing operations often result in extensive process times due to the dependency of the resulting surface topography on the cutting parameter, e.g., the feed per tooth, fz. To overcome this dependency, special tool shapes, called wipers, have proven themselves in the field of turning. This paper presents the transfer of such tool shapes to solid carbide milling tools for micromachining. In this context, a material removal simulation (MRS) was used to investigate promising wiper geometries for micro end mills (d = 1 mm). Through experimental validation of the results, the surface topography, the resulting process forces, and tendencies in the residual stress state were investigated, machining the hot work tool steel (AISI H11). The surface-related results show a high agreement and thus the potential of MRS for tool development. Deviations from the experimental data for large wipers could be attributed to the non-modeled tool deflections, friction, and plastic deformations. Furthermore, a slight geometry-dependent increase in cutting forces and compressive stresses were observed, while a significant reduction in roughness up to 84% and favorable topography conditions were achieved by adjusting wipers and cutting parameters.