List Files

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

Annotations declare readOnlyHint=true, destructiveHint=false, idempotentHint=true. The description adds useful behavioral context: it returns metadata (ID, filename, size, purpose, creation timestamp) and supports pagination and filtering. This goes beyond annotations without contradiction.

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 two sentences: first states the core purpose with key features (pagination, purpose filter), second enriches with return details and filter example. No wasted words, front-loaded, and structured for quick comprehension.

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 tool's 5 parameters, no output schema, and strong annotations, the description adequately covers the listing operation, return metadata, and filtering. It is missing explicit mention of pagination mechanics (cursor usage) but the schema covers that. Overall sufficient for the tool's complexity.

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%, so the baseline is 3. The description adds meaning to the purpose parameter with examples ('assistants', 'fine-tune', 'batch') and mentions pagination in the first sentence, but does not significantly extend beyond the schema's already clear parameter descriptions.

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 title 'List Files' and description 'List all files in your OpenAI project with pagination and optional purpose filter' clearly state the verb (list), resource (files), scope (project), and key features. This effectively distinguishes it from sibling tools like retrieve_file or upload_file.

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 explains what the tool does but does not provide guidance on when to use it versus alternatives (e.g., retrieve_file for a single file, or vector store file lists for scoped listings). No exclusions or context for selection are given.

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