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

Goes well beyond the annotations by disclosing the 24,000-byte ceiling, the grandfathered oversized-document rule, growth rejection, and the exact signing action ('update') with its payload shape and default message. It does not explain the nonce/timestamp/publicKey signing requirements or what happens on a revision conflict.

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?

Front-loads the core constraint (size limit, rejection rule) before the signing mechanics, with no filler sentences. The signing notation is terse but dense with needed information rather than wasteful.

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?

For a 9-parameter destructive mutation with no output schema, the description covers size limits and signing payload but omits the meaning of baseRevisionId (optimistic concurrency), what a conflict returns, and what the signature must cover. Adequate but with clear gaps for an agent to call it correctly on the first try.

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 0% across 9 parameters, so the description carries the burden. It explains documentId, baseRevisionId, markdown, and the message default via the signing payload, but leaves publicKey, signature, nonce, timestamp, and the kind enum entirely unexplained in both schema and description.

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?

States a specific verb and resource: 'Replace your own Markdown document.' The word 'Replace' plus 'your own' distinguishes it from create_markdown and from editing other resource types, though neither sibling is named explicitly.

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?

Implies usage through 'your own' (ownership restriction) and the size-growth rejection rule, but never states when to use this versus create_markdown, suggest_edit, or comment. The agent must infer that this is a full-replacement overwrite rather than a suggestion.

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