chatgpt_upload_files

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

With no annotations provided, the description carries the transparency burden. It discloses required user authorization, absolute path requirement, and the non-automatic prompt-sending behavior. These are meaningful behavioral traits beyond the schema, though it could say more about error handling or size limits.

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 only three short sentences, each adding essential information: the action, the path constraint, and the key behavioral clarification. No filler or redundancy, and it is front-loaded with the primary purpose.

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?

For a simple 1-parameter upload tool with no output schema and no annotations, the description covers the necessary contextual details: authorization, absolute paths, and the no-auto-send behavior. It is sufficiently complete for this complexity level, though a note on success/error behavior would be a minor addition.

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?

The schema already describes the 'files' parameter as absolute paths (100% coverage). The description repeats the absolute path requirement but adds no significant new parameter-level detail. Baseline 3 is appropriate given high schema coverage.

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 the action ('upload local files') and the target resource ('current ChatGPT conversation'), and explicitly differentiates from sibling tools by noting it does not automatically send a prompt. This is a specific verb+resource pair with clear scope.

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 sets a clear usage context: only for local files explicitly authorized by the user, and it mentions the requirement of absolute paths. It does not explicitly name alternatives or when-not-to-use, but the 'does not auto-send prompt' clause implicitly advises that prompt sending needs a separate tool, which is helpful.

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