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

With no annotations, the description carries the full burden and does well: it discloses the state mutation (back to sent), the 14-day constant, the preserved signatures, the signers-in-order limitation to the current stage, and the cost. Missing are failure conditions (what happens if the document is not expired) and any permission requirements.

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?

One dense sentence that front-loads the primary action (new deadline), then the side effects (status reset, resend scope), then the preservation guarantee and cost. No 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?

For a single-parameter mutation tool with no annotations and no output schema, the description covers the state transitions, recipient targeting, and data preservation well. It omits the return value and error behavior, which an agent would want before calling.

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?

Only one parameter (id) at 0% schema description coverage; the description implies it identifies the expired document but never states that it is the document ID or its type. Minimal but inferable from context.

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 (extend an expired document) plus the concrete mechanics: new deadline 14 days out, status back to sent, fresh link to unsigned signers. This is unmistakably distinct from void_document, remind_document, and send_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?

The precondition ('expired document') clearly selects this tool over remind_document or send_document, and the 'Free' note signals a cost-motivated choice. It stops short of explicitly naming the alternative to use when the document has not yet expired.

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