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This paper addresses the common issue of the "Send to Compressed Folder" function failing in Windows systems, based on the best answer from technical Q&A data. It deeply analyzes the impact of file path length limitations on compression functionality. The article begins by introducing the problem through user cases, explaining the correlation between zipfldr.dll registration failure and path length restrictions, then systematically explores the technical principles of Windows file system path length limits (MAX_PATH) and their effects on compression operations. Through code examples and step-by-step instructions, it provides multiple solutions including shortening paths, using alternative compression tools, and modifying registry settings, comparing their pros and cons. Finally, the paper summarizes technical recommendations for preventing such issues, covering best practices in path management and system configuration optimization, offering comprehensive technical reference for system administrators and general users.