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This article addresses common issues when executing JAR files with multiple dependencies in Windows environments, particularly the ClassNotFoundException caused by conflicts between -jar and -cp parameters. Based on analysis of Q&A data, it highlights the Maven Appassembler plugin as the optimal solution for automatically generating startup scripts to simplify classpath management. The article explains the limitations of traditional command-line approaches, compares path separator differences across operating systems, and provides configuration examples and deployment workflows for the Appassembler plugin. Additional alternatives, such as manual classpath construction and wildcard usage, are also discussed to offer comprehensive technical insights. The goal is to assist developers in efficiently deploying Java applications while avoiding common pitfalls in dependency management.