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

Goes well beyond the annotations: it discloses the admin-role requirement, that the same id/body are reused so receivers deduplicate, that the attempt is recorded with `trigger: replay`, and that each call re-sends (consistent with idempotentHint=false). The phrase 'Ignores the event's expiry, not a disabled endpoint' is a valuable constraint but is worded cryptically and does not spell out the resulting error.

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?

Dense but front-loaded: the core action leads, followed by payload semantics, logging side effect, edge-case constraint, and auth requirement. Every clause contributes, though the 'not a disabled endpoint' fragment could be tightened.

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 two-parameter mutation-style tool with no output schema, the description covers the essential operational context: auth requirement, repeat semantics, dedup behavior, and logging. Only the failure mode for disabled endpoints or unknown event ids remains unstated.

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%, so both parameters are already documented; the description only reiterates that `eventId` comes from list_webhook_events and adds no format or lookup detail beyond the schema. Baseline 3 is appropriate when the schema carries the parameter burden.

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+resource ('Deliver a webhook event again') and ties the resource to its identifying source (`eventId` from list_webhook_events). An agent can tell this apart from list_webhook_events and test_webhook_endpoint without opening a schema.

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 clear preconditions: an existing event id, admin role, an enabled endpoint, and it notes expiry is ignored. It does not explicitly contrast itself with the sibling test_webhook_endpoint, which also pushes a webhook, so the alternative-selection guidance is incomplete.

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