This dissertation examines the restructuring of a pre-Columbian Maya community amid political decentralization and climatic discontinuities during the tenth century AD. Notwithstanding highly seasonal rainfall and the near absence of natural surface water in the Puuc region of the northern Maya Lowlands, communities sustainably managed available water resources to cultivate the region’s rich soils and harvest its forest products from the Middle Formative (ca. 800‒450 BC) through the Terminal Classic (ca. AD 800‒950). Ultimately, after more than a century of persistent dry conditions and a series of multi-year droughts, the region depopulated. Sociopolitical and economic reorganization in the Puuc during the late Terminal Classic is evidenced by a building type known as the C-shaped structure—a horizon marker for the Terminal Classic to Postclassic transformation in the northern Maya Lowlands. However, the lack of visibility and architectural variability of this building type have led to diverse interpretations. This research addresses these ambiguities through the extensive archaeological investigation of the Grupo Chanchich—a grouping of C-shaped structures at the site of Huntichmul. Survey and analysis of the architectural morphology and context of Puuc C-shaped structures provides a comparative framework for the evaluation of the Grupo Chanchich. Detailed examination of the Grupo Chanchich built environment and artifact assemblage, including geochemical characterization of obsidian artifacts, informed interpretations of the chronology and function of the group, as well as intra- and inter- regional interactions of the late inhabitants of Huntichmul. The prevalence of Cehpech pottery in construction fill and the use and/or reutilization of worked stone characteristic of Puuc masonry architecture support a late Terminal Classic construction of the Grupo Chanchich, and the paucity of Postclassic pottery suggests its abandonment no later than the tenth century AD. Recent examinations of lidar imagery demonstrate that Grupo Chanchich is not unique; it is one of many C-shaped Structure Groups (CSSGs) in the Maya Lowlands. Shared formal architectural grammar suggests a level of complexity and regional integration amid the breakdown of Classic Maya sociopolitical institutions. Investigation of additional CSSGs will elucidate the nature of this interaction and confirm whether these groups represent marketplace infrastructure.