The continued state of extreme temperatures spanning multiple days is referred to as marine heatwave, an acute event in the coastal ecosystem. The summer of 2023 featured intense and prolonged marine heatwave events in the Gulf of America. Despite the existence of such a large-scale event, the sea surface temperature in the coastal region of the Mississippi Bight was protected from the extreme conditions. This study uses atmospheric and oceanic surface and subsurface observations and reanalysis data over the shelf in this region to understand the processes that lead to these relatively cooler conditions. An anomalously extended period of the southwest seasonal wind conditions proved to be key in driving a season-long upwelling event in contrast to more typical synoptic-scale changes in conditions. However, the cooling efficiency of the upwelling winds is limited by the source of cold water on the shelf. Despite a relatively high slope burger number, the onshore flow of bottom water was a persistent feature throughout the duration of the event, contributing to the coastal cooling. Understanding the dynamics associated with such region extreme upwelling events, as well as sources of cooler water, are critical for predicting coastal responses in a changing climate.