Over a two-month period, contributed to the macports/macports-ports repository by delivering advanced search enhancements and modernizing Python dependencies. Developed and enabled the PCRE-based regex variant as the default for ripgrep, incorporating an iconv dependency to support robust text processing and character encoding. This improved search accuracy and usability for developers working with large codebases. Subsequently, focused on security and stability by updating py-awscrt and py-awscli2 packages, aligning with upstream changes and reducing vulnerability exposure. Work emphasized Python, dependency management, and package management, with careful attention to traceability, compatibility, and future extensibility within the MacPorts ecosystem.