Developed and hardened port-aware URL generation for the ai-shifu/ai-shifu repository, addressing deployment challenges behind Nginx proxies on non-standard ports. Leveraging Python and Nginx configuration skills, implemented logic to correctly propagate the X-Forwarded-Port header and updated backend request origin handling to ensure URLs include the appropriate port when necessary. Expanded automated test coverage to validate both standard and non-standard port scenarios, resolving a persistent issue where URLs dropped non-standard ports and caused misrouting. This work improved deployment reliability and user experience for application previews, demonstrating a methodical approach to backend development and API integration within complex proxy environments.