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

Goes well beyond annotations: it names the destroyed artifact (the old signing token, invalidated immediately), the one-time-only exposure of the new token, the downstream breakage (failed signature verification), and the exact two-call confirmation protocol. The destructiveHint annotation is confirmed and substantially enriched 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?

Three sentences, zero filler, and the highest-impact fact (immediate invalidation, one-time return) is front-loaded ahead of the confirmation mechanics. Every sentence earns its place.

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 non-idempotent mutation with no output schema, the description supplies the return shape (summary + confirmToken), the call protocol, and the consequence of inaction. The only residual gap is webhookId semantics, undocumented in schema and description alike.

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 67%: confirmToken is documented in both schema and description (the description reinforces that it must come from a prior call with the same arguments), but webhookId has no description anywhere and the description does not clarify it either. Baseline 3 is appropriate since the schema carries most of the load.

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+resource (regenerate a webhook's auth token) and immediately defines the effect: the old signing token is invalidated and the new one is returned once. This is clearly distinguishable from sibling webhook tools such as update_webhook, test_webhook, and retry_webhook_delivery.

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?

Explains the required operational context: the receiver must be updated or deliveries will fail verification, and the two-step summary/confirmToken flow is spelled out. It does not explicitly contrast with update_webhook or state prerequisites (permissions, plan tier), 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.