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. Extremely short, subcycle electromagnetic field waveforms are rapidly emerging as powerful tools for ultrafast optics and photonic technologies 1-3 , enabling an unprecedented, subfemtosecond time resolution in laser spectroscopy 4,5 and an ultimate, subcycle precision in lightwave sculpting 6,7. Subcycle field waveforms are not unusual in terahertz technologies 8 , where such waveforms are generated as a result of optical rectification 9,10 , providing means for time-domain spectroscopy 11 , terahertz sensing 12 , and sub-quarter-cycle engineering 13. Terahertz field cycles are, clearly, too long to be relevant as probes for ultrafast dynamics in molecules, let alone the attosecond dynamics of electron wave packets and electron excitations in atoms and solids. Yet, the significance of the early work on subcycle terahertz field transients 8,9,14 is hard to overestimate-we owe it much of our understanding of fundamental properties of subcycle pulses and the universal tendencies in their unusual propagation dynamics. Optical methods of subcycle pulse generation rely on coherent field waveform synthesis 2 operating with high-order harmonics 15 , multiple Raman sidebands 16-19 , frequency-shifted supercontinua from hollow-core fibers 1,6 , and cascaded parametric amplification 20. As a promising alternative, anomalous-dispersion-assisted multioctave supercontinuum generation in solid materials 21 and guided-wave soliton self-compression (SSC) 22,23 can help create efficient sources of subcycle pulses covering a broad range of frequencies and peak powers. Here, 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. Optical shock waves are inevitable when the pulse duration of a field waveform approaches the field cycle 24. As their archetypical signature, optical shock waves tend to steepen the tail of the pulse, blue-shifting its spectrum 25. In special regimes of three-dimensional free-beam propagation, optical shock waves have been shown to force field waveforms to self-compress to subcycle pulse widths 26. Ordinarily, however, when building up via waveguide short-pulse evolution, optical shock waves do not lead to pulse shortening as a whole, giving rise to pulses with sharper trailing edges and asymmetric supercontinua. Still, our analysis presented in this paper shows that, when coupled to soliton self-compression an optical shock facilitates the generation of extraordinarily short field...