rotate_webhook_endpoint_secret

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

Adds substantial context beyond the annotations: the 24-hour signature overlap window, the required permission scope, the instruction to update the receiver's secret configuration, and the secret-handling prohibition. The destructive/openWorld/idempotent hints are corroborated rather than merely restated.

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 action and its gate in the first sentence, then layers prerequisites, overlap behavior, and idempotency guidance. Slightly dense and contains a redundant restatement of the schema's const:true, but every sentence carries useful information.

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, authorization-gated rotation with a full output schema, the description covers the safety profile, permission requirement, blast radius (24-hour overlap), and retry semantics. Nothing an agent needs to invoke it correctly 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; the description still adds operational meaning by tying confirm_rotation to explicit operator authorization and clarifying that idempotency_key is a single-intent retry token, which the schema phrasing only partly conveys.

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 ('Rotate the signing secret') with an added scope/gating constraint, which separates it cleanly from siblings like update_webhook_endpoint, test_webhook_endpoint, and list_webhook_endpoints.

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?

Gives explicit preconditions (operator authorization, confirm_rotation:true, webhook.manage scope) and post-incident guidance (reuse the exact idempotency_key after an uncertain mutation). It does not name an alternative tool for the non-rotation case, so it stops short of full when/when-not routing.

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