Upload file

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

The annotations already declare this as a non-read-only, open-world, non-idempotent, non-destructive operation. The description adds useful behavioral context beyond those hints: accepted file types, a 20 MB size cap, and the fact that it returns a file_id. It does not mention auth or rate limits, but with annotation coverage this is a solid disclosure level.

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 front-loaded with the action and key constraints, and every sentence carries useful information. The long parenthetical format list is somewhat cumbersome but justified for an upload tool, so it is concise enough without being exemplary.

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 no output schema, the description appropriately fills the return-value gap by stating that it returns the file_id. It also covers formats and size limits, which are important for correct invocation; the main remaining gap is that it does not explain how to choose among url, path, and content_base64, though the schema covers those fields.

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 100%, so all four parameters are already documented in the schema. The description only adds a small path hint that largely repeats the schema's "Absolute path of the file on this computer" text and does not clarify mutual exclusivity among url, path, and content_base64; baseline 3 is appropriate.

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 gives a clear verb and resource ("Upload a file") and adds concrete scope: supported formats, the 20 MB limit, intended downstream uses, and the returned file_id. It is specific enough to distinguish this as the file-ingestion tool, but it does not explicitly contrast itself with siblings such as convert_file or create_document.

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 states clear use contexts: upload to convert or edit the file, or to use it as a source. However, it does not name alternatives or exclusions, such as when to use upload_file versus convert_file or create_document, so it falls short of full routing guidance.

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