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

Goes far beyond the annotations by disclosing the single-use secret return (the whsec_ secret is returned ONCE), the HMAC verification recipe with the exact signature header format, and the auth level required. The annotations already flag destructive and open-world behavior, and the description adds operational details an agent needs to correctly consume the registration.

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 compact sentences, front-loaded with purpose and followed by implementation-critical caveats (secret returned once, signature verification, auth level). The signature formula is dense but earns its place because an agent calling this must capture the secret and document the verification contract.

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?

Given the tool has an output schema (so returns need not be explained), the description supplies the secret-return lifecycle, the signature verification scheme, and the auth prerequisite. An agent can register the webhook and understand how to verify deliveries without external documentation.

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 both parameters are documented (url as HTTPS endpoint, events as an array with defaults and allowed values). The description adds the event taxonomy and "https" constraint but does not add syntax or format semantics beyond the schema, 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 precise verb and resource ("Register an https URL to receive job lifecycle events") and enumerates the exact event types delivered. Clearly distinguishes it from webhooks_list, webhooks_delete, and webhook_test by naming what registration actually does.

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?

Offers "push instead of polling" as a rationale and states the "Requires owner/admin" prerequisite, which is useful context. However, it never explicitly says when to use webhooks_set vs. webhook_test, or that webhooks_list/delete exist for managing existing hooks, so an agent must infer the routing.

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