upload_file

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

With no annotations, the description carries the full burden of behavioral disclosure. It mentions 'zero token cost' and 'path-based', but does not disclose overwrite behavior, permission requirements, return values, or error handling. This is a significant gap for a mutation tool.

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, front-loaded with the core action and followed by two concise, relevant tips. Every word earns its place with no redundancy or filler.

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?

The schema thoroughly documents parameters, but with no output schema or annotations, the description should state what a successful upload returns (e.g., success flag or task ID) and what failure modes exist. The description leaves these unaddressed, making it adequate but not fully complete.

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 practical value by recommending async mode for large files, which is not tautological and helps the agent choose the right parameter setting. Other parameters are already well-documented in the schema.

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 uses a specific verb and resource: 'Upload local file to remote server'. It clearly distinguishes from sibling upload_directory by specifying 'file' and adding 'path-based', making the scope unambiguous.

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 gives a clear conditional tip, 'Use async mode for large files', which guides parameter selection. However, it does not explicitly state when to prefer this over alternatives like upload_directory or write_file, though the name implies the distinction.

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