According to the “adaptation cycle” theory (Holling and Gunderson 2001), human adaptation to the changing coastal environment may be enhanced by repeated disaster experiences. However, one might establish a distinction between planned “first order” adaptation processes and spontaneous “second order” social and economic adaptation processes (Birkmann 2011). This paper aims to investigate the coastal Mississippi case-study to test the factors that help explain why “second order” adaptation is more efficient than planned “first order” adaptation. Coastal Mississippi has experienced two devastating hurricane strikes from Camille (1969) to Katrina (2005). For this reason, this case-study is focused on investigating theories about adaptation and mitigation policies versus coastal hazards. This paper reviews the Mississippi Coast’s experience with an eye to lessons learned and lessons lost from these catastrophic events. The comparison between the disaster responses during Camille and Katrina displays significant progress. However, comparing the post-Camille reconstruction and the ongoing post-Katrina rebuilding process also shows evidence of the difficulty of learning lessons fromdisasters. This is vividly underscored when land developers and home owners rebuilt in vulnerable locations. Local interests strongly reject options like “potential buy-out areas” and demand instead an increased protection, eventually under the guise of soft environmental restoration programmes whenever structural options are not available. Unfortunately, the climate-change driven sea-level rise thwarts these mitigation strategies on the long run. For this reason, the next major hurricane-induced storm surge could well cause another disaster, similar to or worse than those already caused by Camille and Katrina, except if a strategic retreat from the shoreline is actually implemented. Nowadays, market forces seem more efficient in triggering a “second-order” urban adaptation process than faltering planners.