Simao Caixas enhanced the search functionality in the ppy/osu repository by improving how song titles with punctuation boundaries are matched. Focusing on backend development with C#, Simao expanded the IsolatedPhrase matching logic to recognize Unicode punctuation and whitespace as valid boundaries, ensuring that titles surrounded by quotes or punctuation are accurately found. The update addressed a specific bug where search results could be missed if punctuation enclosed a quoted phrase. Simao reinforced the solution with targeted unit tests, validating the new boundary behavior and maintaining code quality through successful CI runs, ultimately improving search reliability and user experience for the project.