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

Adds real context beyond the annotations: it retries the same event as a new attempt, returns whether it arrived plus the HTTP status, and requires owners/admins. This corroborates idempotentHint=false rather than contradicting it. It stops short of mentioning rate limits or what happens on repeated retries, so it is not exhaustive.

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?

Three tight sentences, front-loaded with the triggering scenario and ending with the exclusion. A small deduction for the slightly garbled phrasing 'a delivery a webhook or chat channel missed sent again', which takes a reread.

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 2-parameter mutation with no output schema, the description covers the trigger, the alternative, the auth requirement, and return values. Nothing an agent needs to invoke or interpret the result is missing.

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 description coverage is 100%; both params already explain where the id comes from (list_webhooks, list_webhook_deliveries). The description adds no parameter-level detail such as whether a name or id is preferred or how ambiguity is resolved, so baseline 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 (send again) and resource (webhook delivery), and explicitly distinguishes itself from the sibling test_webhook. The 'as the Webhooks page's Retry does' framing anchors the semantics for an agent familiar with the UI.

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?

Gives the triggering condition ('user wants a delivery a webhook or chat channel missed sent again, once the endpoint is fixed') and an explicit exclusion with the correct alternative ('Not for a test event (use test_webhook)'). Both when-to-use and when-not-to-use are covered.

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