Jean Ibarz developed multi-file attachment support for task messages in the CLI tools of both the a2aproject/a2a-samples and google/A2A repositories. Using Python, Jean implemented a loop-based input system to collect multiple file paths, encoding and appending each file to the outgoing message. The solution included robust error handling for missing or unreadable files, improving reliability and user experience. By standardizing this feature across repositories, Jean enhanced cross-repo consistency and collaboration. The work demonstrated depth in CLI development, error handling, and file management, addressing a common workflow friction point and delivering a more seamless process for attaching supporting documents.