This study reports on a direct approach of quantitatively probing the nanotribological response of chemically end-grafted polyions. A combination of a quartz crystal microbalance with dissipation and atomic force microscopy, in the now well established colloidal probe mode, was utilized to investigate the stimuli-induced lubrication behavior between poly(2-(dimethylamino)ethyl methacrylate) grafts on gold. Force and friction measurements showed reversible transitions of up to an order of magnitude difference induced by varying the solvent conditions. The greatly enhanced lubrication observed at low pH was attributed to the formation of a repulsive, highly charged, hydrated cushion. At high pH the friction was significantly increased. The system turned attractive above the lower critical solution temperature with a small friction reduction interpreted as being due to nanoscopic flattening at the interfacial boundary.