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

Even with annotations present, the description adds meaningful behavior not captured there: the signing_secret is returned only once and must be used to verify the x-hires-signature-v2 header. This is important operational information for the agent. No contradictions with 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?

Two concise sentences containing only high-value information: the action, the scope, and the critical one-time secret behavior. It is front-loaded and has no filler.

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 appropriately explains the key return value (`signing_secret`), that it is returned once, and how it should be used. For a two-parameter create tool with complete schema coverage, this is sufficient.

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?

The input schema already covers both parameters at 100%, including the HTTPS-public-host restriction on `url`. The description adds no additional parameter semantics, so baseline score of 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 uses a specific verb, 'Register an HTTPS webhook', names the resource (a job webhook), and specifies its event scope ('this job's events'). This clearly distinguishes it from generic webhook tools like hires_create_webhook and from read/list webhook tools.

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 clear contextual scoping: it is for registering a webhook for a specific job's events. It does not explicitly name `hires_create_webhook` as the alternative for non-job webhooks, but the 'for this job's events' framing is clear enough for an agent to decide when to use this tool.

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