This analysis follows the development of ssh-auth-cmd, a tool that allows chaining multiple SSH authentication sources. Written primarily by Claude AI under human guidance, the project serves as a fascinating case study in AI-assisted development. The article documents the complete conversation history, including breakthrough moments like discovering how to constrain AI for clean refactoring, handling licensing questions for AI-generated code, and the iterative feedback process that led to production-ready software. The project demonstrates how AI can handle substantial code generation while humans provide critical architectural oversight and quality control.