The evolution of an undular bore and its associated wind shift, spawned by the passage of a shallow surface cold front over the Southern Great Plains of the United States, is examined using surface and remote sensing observations along with output from a high-resolution numerical model simulation. Observations show that a separation between the wind shift and thermodynamic properties of the front was induced by the formation of a bore over south-central Kansas around 0200 UTC 29 November 2006. By the time the front-bore complex passed through Lamont, Oklahoma, approximately 4 h later, the bore had reached its maximum intensity and its associated wind shift preceded the trailing baroclinic zone by 20 min. Within several hours the bore decayed and a cold frontal passage, characterized by a wind shift coincident with thermodynamic properties was observed at Okmulgee, Oklahoma. Thus, a substantial transformation in both the structural and dynamical characteristics of the bore as well as its relationship to the parent surface front occurred during a short period of time.The details of this evolution are examined using output from a finescale numerical simulation, performed using the Weather Research and Forecasting (WRF) model. Analysis of the output reveals that as the bore advanced southeastward it moved into a region with a weaker surface stable layer. Consequently, the wave duct that had supported its maintenance steadily weakened resulting in dissipation of the bore. This circumstance led to a merger of the surface temperature and moisture boundaries with the orphaned wind shift, resulting in the cold frontal passage observed at Okmulgee.