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

Beyond the annotations, it discloses the 24-hour overlap window for old signatures, the need to update receiver secret configuration, the requirement to never leak secrets in logs or prompts, and the webhook.manage permission. This turns the destructiveHint into actionable behavioral context without contradicting the annotations.

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 dense and front-loaded with the core action and its precondition. Every sentence adds operational or safety value, though authorization is mentioned twice ('Requires webhook.manage' and 'same ... authorization'), a minor redundancy in an otherwise tight definition.

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 destructive webhook secret rotation, the description covers authorization, side effects, security constraints, idempotency, and includes a docs link; the output schema removes the need to document return values. It is slightly incomplete only because expected_revision's concurrency/optimistic-locking role is left to inference.

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%, so the description must carry the parameter-semantics burden. It explains confirm_rotation as the explicit consent gate and gives meaning to idempotency_key through the retry instruction. However, endpoint_id and expected_revision are left undocumented beyond their names, so compensation is only partial.

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 opens with a specific verb and resource: 'Rotate the signing secret'. This clearly distinguishes the tool from sibling webhook tools like update_webhook_endpoint or test_webhook_endpoint, whose purposes are different. It also makes the safety-gated nature of the operation explicit.

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 strong usage conditions: rotate 'only with explicit operator authorization and confirm_rotation:true', and reuse the exact idempotency_key after an uncertain mutation. It does not explicitly name alternatives or state when not to use the tool, so it falls just short of full when/when-not guidance.

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