We identify an unusual regime of ultrafast nonlinear dynamics in which an optical shock wave couples to soliton self-compression, steepening the tail of the pulse, thus yielding self-compressing soliton transients as short as the field sub-half-cycle. We demonstrate that this extreme pulse self-compression scenario can help generate sub-half-cycle mid-infrared pulses in a broad class of anomalously dispersive optical waveguide systems.