With traditional powers of Egypt and Hatti diminishing at the end of the Late Bronze Age, the sitz im leben in Canaan shifted as well. The changes in the Late Bronze-Iron Age transition reflect a shifting power structure considerably different from those present in the days of Egyptian hegemony. Merenptah’s attack on Canaan, as noted in his Victory Stele, signaled that shift. Local level power structures were affected by Merenptah’s victory, while the traditional elites weaken with internal strife following Merenptah. With the Canaanite cities of Ashkelon and Gezer captured and plundered, this may have destabilized the local region leading to ramifications for other sites/ people groups. The impetus of this study begins with Merenptah who reigns at the end of the 13th century form 1213-1203BC, the end of the Late Bronze IIB. This establishes the terminus post quem for this study and a focus on Canaanite sites at this critical juncture. A thorough review of these sites, which span both the Coastal Plain the western portion of the Shephelah and a few beyond, show an emerging pattern of destroyed sites emerging in the LB IIB, only two sites of which can be attributed to Merenptah (textually at least).This study will also incorporate newer data coming from the recent excavations at Gezer considering the pharaoh’s link to this site. The questions this study investigates is both the manner or classification of destruction in these sites and to whom to attribute these destruction levels. This study provides contextual and historical background for the book of Joshua and Israel’s entry into Canaan.