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This comprehensive technical article explores various methods for executing JAR files through double-click in Windows operating systems. Beginning with fundamental concepts of JAR files and their executable requirements, the paper thoroughly analyzes file association configuration procedures, including traditional folder options setup and alternative approaches for modern Windows versions. The discussion extends to diagnostic techniques for common issues such as Java environment configuration, manifest file specifications, and distinctions between javaw and java executables. Practical alternatives including batch files and third-party tools are presented, ensuring readers can select optimal solutions based on their specific environment.