Title: Enhancing SQL-Based Cloud Application Reliability Through Proactive Telemetry Analysis Using Azure AppInsights Abstract: This paper presents a novel approach to proactive performance and availability monitoring for SQL-dependent cloud applications hosted on Microsoft Azure. The study introduces an integrated monitoring framework utilizing Azure Application Insights to capture, analyze, and diagnose anomalies in transactional workloads involving SQL databases and web APIs. Through empirical evaluation using real-world data from a governmental interoperability platform, the research demonstrates how telemetry-driven insights can preemptively identify SQL-related failures, dependency breakdowns, and performance degradations. Results indicate significant improvements in mean time to detection (MTTD) and resolution (MTTR) for database-linked incidents, supporting the argument that cloud-native monitoring tools are essential for maintaining SQL application reliability in SME environments. The framework further contributes a comparative analysis of on-premises versus cloud monitoring efficacy, emphasizing the role of predictive analytics in sustaining service-level agreements (SLAs) for data-centric applications.