upload_file_to_chat

Does the description disclose side effects, auth requirements, rate limits, or destructive behavior?

With no annotations provided, the description carries the full burden of behavioral disclosure. It describes the uploading process and the two modes of providing file data, but does not mention any side effects, authentication needs, rate limits, or what happens if the chat is invalid or file already exists. The return type is mentioned, but deeper behavioral traits are absent.

Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

Is the description appropriately sized, front-loaded, and free of redundancy?

The description is structured with a brief opening sentence followed by a bulleted list of parameters and a returns note. It is clear and without extraneous text. Slightly more concise phrasing could be used, but overall it is efficient and front-loaded.

Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

Given the complexity (5 parameters, mutual exclusivity, optional reply-to), the description covers the essential behavior and return format. It does not discuss error cases, file size limits, or supported file types, but the presence of an output schema (per context signals) reduces the burden on the description for return value details. The description is largely complete for a file upload tool.

Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

Schema description coverage is 0%, so the description must fully explain each parameter. It does: chat_id, file_path, file_content, filename, and reply_to_message_id. It explains the mutual exclusivity of file_path and file_content, and the requirement for filename when file_content is set. This adds significant meaning beyond the bare schema.

Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

Does the description clearly state what the tool does and how it differs from similar tools?

The description clearly states 'Upload a file to a chat,' which is a specific verb+resource combination. It distinguishes from sibling tools like send_message (for text) and download_post_attachment (for downloading). The title 'upload_file_to_chat' directly maps to the described action.

Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

Does the description explain when to use this tool, when not to, or what alternatives exist?

The description provides explicit guidance on when to use file_path vs file_content, noting their mutual exclusivity and the filename requirement when file_content is used. It does not explicitly mention when not to use this tool compared to siblings, but the parameter explanations help the agent decide. Missing context on file size limits or format constraints.

Agents often have multiple tools that could apply. Explicit usage guidance like "use X instead of Y when Z" prevents misuse.