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

Annotations already declare destructiveHint=true, idempotentHint=false, and openWorldHint=true, so the risk profile is covered. The description adds the useful precondition ('after fixing the receiver') and the 7-day lookback bound, but says nothing about duplicate delivery to the receiver or what the operation returns/whether it is rate-limited.

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?

One compact sentence with the scope and the operational precondition front-loaded; nothing is redundant.

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, non-idempotent mutation with no output schema, the description covers the trigger condition and window but leaves the agent guessing about the result (how many events replayed, failure handling) and about duplicate-delivery side effects.

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 the schema already documents id, since, and until. The description contributes one extra piece of semantics not in the schema — the maximum 7-day window — which is the baseline-plus case for a fully documented schema.

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?

Specific verb ('re-send') plus resource ('every event that failed to reach a webhook endpoint') plus scoping window. It is distinguishable from list_webhook_deliveries or test_webhook, but it never differentiates itself from the sibling replay_event, which an agent could easily confuse it with.

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?

'after fixing the receiver' gives one precondition, and the window defaults are stated, but there is no explicit guidance on when to prefer this over replay_event, test_webhook, or list_webhook_deliveries to inspect failures first.

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