A single-degree-of-freedom active cutting fixture is employed to reveal and analyse the hysteretic nature of the lobed stability boundary in a simple machining experiment. Specifically, the seventh stability lobe of a regenerative cutting process is mapped using experimental, analytical, and computational techniques. Then, taking width of cut as a control parameter, the transition from stable cutting to chatter is observed experimentally. The cutting stability is found to possess a substantial hysteresis so that either stable or chattering tool motions can exist at the same nominal cutting parameters, depending on initial conditions. This behavior is predicted by applying nonlinear regenerative chatter theory to an empirical characterization of the cutting force dependence on chip thickness. Time-domain simulations that incorporate both the nonlinear cutting force dependence on chip thickness and the multiple-regenerative effect due to the tool leaving the cut are shown to agree both qualitatively and quantitatively with experiment.