Real-data simulations have been conducted for several DEEPWAVE intensive observing periods (IOPs). The results suggest that horizontal shear associated with the stratospheric polar night jet refracts the gravity waves and leads to propagation of waves significantly downwind of the South Island of New Zealand. These waves have been referred to as “trailing gravity waves”, since they are found predominantly downwind of the orography of the South Island and the wave crests rotate nearly normal to the mountain crest. Observations from the G-V, remote sensing instruments (AMTM, Rayleigh lidar), and the AIRS satellite confirm the presence of gravity waves downwind of the orography in numerous events during DEEPWAVE. The horizontal propagation in the stratosphere can be explained by group velocity arguments for three-dimensional gravity waves in which the wave energy is advected downwind by the component of the flow normal to the horizontal wavevector. We further explore the impact of the shear on gravity wave propagation in COAMPS configured in an idealized mode initialized with a zonally balanced stratospheric jet. The idealized results confirm the importance of horizontal wind shear for the refraction of the waves. Furthermore, the zonal momentum flux minimum is shown to bend or refract into the jet in the stratosphere as a consequence of the wind shear.