chatgpt_upload_files

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

With no annotations, the description carries the behavioral burden and discloses key traits: upload only, no automatic prompt submission, and the requirement for absolute paths. It states an authorization constraint ('explicitly authorized by the user'), which goes beyond the basic operation, though it omits details like file-size limits or error behavior.

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?

Three short sentences, each carrying distinct information: the operation, the path constraint, and a critical behavioral caveat. There is no filler or repetition.

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 single-parameter upload tool, the description covers the purpose, invocation constraint, and a key consequence (no prompt is sent). It is complete enough for an agent to select and call it correctly, though the lack of an output schema means return/error behavior is not described.

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 coverage is 100% and the schema already describes 'files' as a list of absolute paths. The description reinforces this requirement and adds context about local/user-authorized files, but it does not materially extend the parameter semantics beyond what the schema already provides.

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 names a specific verb ('upload'), a precise resource ('current ChatGPT conversation'), and the scope ('local files explicitly authorized by the user'). This distinguishes it from sibling tools like chatgpt_add_file_to_project, which targets projects rather than the active conversation.

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?

It clearly frames when to use the tool: when the user has authorized local files and the target is the current ChatGPT conversation. The caveat 'will not automatically send a prompt' signals that a separate prompt-sending tool is required if a message must follow, although it does not explicitly name the alternative.

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