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

Annotations already declare destructiveHint=true and idempotentHint=true, so the safety profile is known. The description adds genuinely new behavioral detail beyond that: unsent deliveries are discarded, not delivered, and the return is a bare boolean. That is useful operational context an agent cannot get from annotations alone.

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?

Four short front-loaded sentences, each carrying a distinct fact (action, delivery behavior, idempotency, return value). Slightly redundant since the output schema already defines the return, but the sizing is appropriate and there is 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?

For a destructive single-parameter tool with full annotation coverage and an output schema, the description covers the operation, side effects on queued deliveries, retry semantics, and result. Only minor gaps remain, such as authorization requirements or behavior for a nonexistent ID (which 'repeated deletion succeeds' partially implies).

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 with 100% schema description coverage, so the baseline is 3. The description adds no further meaning about the ID (format, source, whether it must be an existing webhook) beyond what the schema states.

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 opens with a specific verb (deletes) and resource (webhook), making the operation unambiguous and easily separable from siblings like delete_proxy or delete_og_config. It does not explicitly name an alternative, but the resource noun does the differentiation work.

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?

'Repeated deletion succeeds' implicitly signals this is safe to retry and usable in cleanup flows, but there is no explicit statement of when to prefer this over other tools or what prerequisite state (e.g., webhook must belong to the caller's account) is required. Usage is implied rather than stated.

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