This study provides a comprehensive analysis of the paddy cultivation sector in the state of Kerala, India, from 2005 to 2020, a period characterized by significant structural transformations. The research addresses the central paradox of a sharp and continuous decline in the area under paddy cultivation occurring concurrently with a steady increase in land productivity. The primary objectives of this paper are to empirically analyse the trends in land utilization, including both cultivated and fallow lands; to examine the divergent trajectories of total production and per-hectare productivity; and to evaluate the profound implications of these trends for the state's food security. The methodology is based on a descriptive and comparative analysis of time-series data compiled from official government sources, including the Kerala Directorate of Economics and Statistics and National Sample Survey reports. The findings reveal a substantial contraction of approximately 25.6% in the cultivated paddy area over the 15-year period. In stark contrast, productivity demonstrated a robust increase of 35.3%, rising from approximately 2,285 kg/ha to over 3,090 kg/ha. Despite these efficiency gains, the state's domestic production has stagnated, consistently meeting only about 10% of its total rice consumption, thereby creating a significant food security deficit. Scenario-based analysis indicates that even under optimistic assumptions of full land utilization and achieving national productivity benchmarks, Kerala cannot attain self-sufficiency. The study concludes that productivity enhancements alone are insufficient to address the state's food security challenges. It underscores the critical need for an integrated policy framework that not only promotes technological adoption and climate resilience but also addresses the underlying socio-economic drivers of land conversion, thereby ensuring the economic viability and ecological sustainability of paddy farming in Kerala.