tailscale_rotate_webhook_secret

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

The description adds significant behavioral context beyond annotations: the old secret is immediately invalidated, the new secret must be saved immediately, and a security warning about response handling. No contradiction with 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?

Two concise paragraphs: first describing the action and critical behaviors, second a security warning. No extraneous content; every sentence adds value.

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?

The description is complete for this simple rotation tool. It explains the return value (new secret), its sensitivity, and the effect on the old secret. No output schema is needed given the clear return description.

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% for the single parameter (webhookId), and the description does not add new details about the parameter beyond what the schema provides. Baseline 3 is appropriate.

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 clearly states the action 'rotate' and the resource 'webhook's secret', with explicit details about the behavior (returns new secret, old invalidated). It distinguishes from sibling tools like delete or update webhooks.

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 usage for secret rotation but does not explicitly state when to use this tool versus alternatives (e.g., update_webhook or delete_webhook). It lacks explicit when-not or alternative tool references.

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