Rotate webhook secret

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

Annotations only supply the generic safety flags (readOnlyHint=false, idempotentHint=false, destructiveHint=false, openWorldHint=true). The description goes well beyond them by disclosing the one-time retrieval constraint, the immediate invalidation of the old secret, and a security note about clients persisting responses to logs and transcripts. This is exactly the behavioral context annotations cannot convey.

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?

Two short sentences plus a labeled SECURITY note; the critical 'save it immediately' warning is front-loaded and every sentence carries unique information. No padding or repetition of the title.

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?

With no output schema, the description correctly compensates by explaining what is returned (the new secret, verbatim) and that it cannot be retrieved again. For a one-parameter mutation tool, an agent has everything needed to call it and handle the result safely.

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?

There is a single parameter (webhookId) with 100% schema description coverage, so the schema fully documents it. The description adds no format, sourcing, or lookup guidance for the ID, so the baseline of 3 applies.

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 a webhook's secret') and clearly distinguishes itself from siblings like tailscale_update_webhook or tailscale_create_webhook by naming the exact mutation being performed on the secret. An agent can select this tool without opening the schema.

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 implies the usage context (you need a fresh secret, so rotate) and warns about the immediate invalidation of the old secret, but it never explicitly says when to choose this over tailscale_update_webhook or why a rotation would be needed. Usage is inferable but not stated or contrasted against alternatives.

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