One of the main limits of productivity during cutting processes is the occurrence of regenerative chatter. Due to these self-excited vibrations, the load capacity of the machine components, the tool as well as the machine performance cannot be fully utilized. There are several methods to stabilize the milling process. One is the use of increased process damping, which results from the contact of the tool’s flank face and the workpiece. The flank wear land naturally increases the contact between tool and workpiece. However, this effect has not been used to increase productivity in milling processes. This paper investigates with experiments and numerical simulations how tool wear affects process stability in milling of aluminum and steel. Therefore slot milling and side milling tests were carried out with tools of various states of flank wear. It could be shown that increasing flank wear allows to raise the depth of cut ap up to 300% in machining aluminum and perform the machining process with a higher productivity.