With a broader intention of producing thin sheet embossing molds, orthogonal cutting experiments of thin workpieces are conducted. Challenges in machining thin workpieces are many: machining induced stress and deformation, fixturing challenges, and substrate effects. A setup involving continuous orthogonal cutting with a single crystal diamond toolof an aluminum alloy (Al6061-T6) workpiece fixtured using an adhesive to reduce its thickness is used to study trends in forces, chip thickness, and to understand to what level of thickness we can machine the workpiece down to and in what form the adhesive fails. There are no significant changes observed in the forces and chip thickness between thick and thin workpieces during the experiments, meaning that the cutting energy required is the same in cutting thick or thin workpieces. The limitation to achieve thinner workpiece is attributed mainly due to the detachment of the thin workpiece by peel-off induced by adhesive failure mode, which occurs during initial chip formation as the tool initially engages with the workpiece. We use a finite element model to understand the stresses in the workpiece during this initial tool engagement when it is thick and when it is thin, as well as the effect of the adhesive itself and the effect of adhesive thickness. Simulation results show that the tensile stress induced by the tool at the workpiece-adhesive interface is higher for a thinner workpiece (45 μm) than a thicker workpiece (150 μm) and higher at the entrance. As such, a thinner workpiece is more susceptible to peel-off. The peeling of thin workpiece is induced when the high tensile stress at the interface exceeds the tensile-at-break value of the adhesive.