Despite significant, steady improvements in the skill of medium-range weather prediction systems over the past several decades, the accuracy of these forecasts are occasionally very poor. These forecast failures are referred to as “busts” or “dropouts”. The lack of a clear explanation for bust events limits the development and implementation of strategies designed to reduce their occurrence. This study seeks to explore a flow regime where forecast busts occur over Europe in association with mesoscale convective systems over North America east of the Rocky Mountains. Our investigation focuses on error growth in the European Centre for Medium-Range Weather Forecasting’s (ECMWF’s) global model during the summer 2015 PECAN (Plains Elevated Convection at Night) experiment. Observations suggest that a close, but varied interrelationship can occur between long-lived, propagating, mesoscale convection systems over the Great Plains and Rossby wave packets. Aloft, the initial error occurs in the ridge of the wave and then propagates downstream as an amplifying Rossby wave packet producing poor forecasts in middle latitudes and, in some cases, the Arctic. Our results suggest the importance of improving the representation of organized deep convection in numerical models, particularly for long-lived mesoscale convective systems that produce severe weather and propagate near the jet stream.