chatgpt_ask

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

With no annotations, the description must disclose behavior but only lists supported features. It omits critical details like state changes to chat history, authentication/login requirements, potential hang or failure modes, and what exactly 'get the assistant response' returns.

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 a single sentence that front-loads the action ('Send a question...'), enumerates key features efficiently, and contains no filler—every clause adds meaningful information.

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?

With 13 parameters and no output schema, the description is underspecified. It does not explain return format, error handling, or how to combine features (e.g., web_search + reasoning), and lacks guidance on prerequisites like login or browser state.

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 covers all parameters with descriptions, so baseline is 3. The description adds a high-level summary mapping capabilities to parameters but does not provide deeper semantics or usage nuances beyond what the schema already states.

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 tool sends a prompt to ChatGPT Web and returns a response, lists key capabilities (web search, reasoning, models, attachments, profiles), and implicitly distinguishes it from siblings like chatgpt_get_latest_response which only retrieves.

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 implies this is the primary ask tool by listing its features, but it does not explicitly state when to use it versus alternatives (e.g., chatgpt_new_chat, chatgpt_get_latest_response) or mention any exclusions—leaving context inferred.

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