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

The description goes well beyond the sparse annotations by disclosing that it is stdio-only, hashes file content, deduplicates by matching content, and returns a ready-to-use file_id. It also explains the critical limitation (cannot read disk over remote/OAuth) that the annotations alone would not convey.

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 dense sentences cover operation, dedup, alternative tools, and downstream usage with no filler. The most important constraint ('stdio MCP only') is front-loaded.

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 complexity, the description fully covers what it does, when to prefer it, when to avoid it, and what to do with the result. The presence of an output schema relieves it from explaining return details, and no necessary behavioral context is missing.

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, but the description enriches the single path parameter by explaining that the path must be a local, client-side file readable by stdio MCP and that its bytes are used for SHA-256 content matching. This adds practical meaning beyond the schema's 'absolute or relative path'.

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 states a precise verb and resource: reads a local path, SHA-256s the bytes, uploads to NexDoc, reuses an existing matching file, and returns a file_id. It also distinguishes this from request_file_upload by transport, and from asset_files by use case, so an agent can tell it apart from siblings.

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?

Explicit when-to-use guidance is present: 'Use this instead of asset_files for large photos' and 'Remote/OAuth MCP cannot read the client's disk — use request_file_upload... instead.' It also chains the tool into the workflow by directing file_ids to create_design or update_design.

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