We report microscale friction experiments for diamond/metal and diamond/silica contacts under gigapascal contact pressures. Using a new nanoprobe technique that has a sufficient dynamic range of force and stiffness, we demonstrate the processes involved in the transition from purely interface sliding at the nanoscale to the situation where at least one of the sliding bodies undergoes some plastic deformation. For sliding of micrometre-sized tips on metallic substrates, additional local plastic yielding of the substrate resulting from tangential tractions causes the tip to sink into the surface, increasing the contact area in the direction of loading and resulting in a static friction coefficient higher than the kinetic during ploughing. This sink-in is largely absent in fused silica, and no friction drop is observed, along with lower friction in general. The transition from sink-in within the static friction regime to ploughing in the sliding friction regime is mediated by failure of the contact interface, indicated by a sharp increase in energy dissipation. At lower contact pressures, the elastic interfacial sliding behaviour characteristic of scanning probe or surface force apparatus experiments is recovered, bridging the gap between the exotic realm of nanotribology and plasticity-dominated macroscale friction.