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

Annotations only cover the generic safety profile (readOnly=false, destructive=false, idempotent=false, openWorld=true). The description adds real behavioral context beyond that: the ten-replay cap per delivery, the requirement that the receiver deduplicate repeated IDs, and the guarantee that the underlying operation is not re-executed or re-charged. This is consistent with idempotentHint=false, since deduplication responsibility is pushed to the receiver.

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 sentences, front-loaded with the action and its defining property, followed by constraints and then the negative scope. Every sentence carries distinct information with no repetition.

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?

With no output schema and a simple two-parameter shape, the description covers everything an agent needs: what is requeued, the required scope, the rate limit, the receiver-side obligation, and the fact that no billing or operation side effect occurs.

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 with their sources ('Stable event ID from get_events' / 'Owned active webhook ID from create_webhook'). The description reinforces the 'owned active webhook' and 'original event ID' constraints but adds no new syntax or format detail, 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 specific verb and resource ('Requeue a known event to an owned active webhook') and adds the key qualifier 'while preserving its original event ID.' This is clearly distinguishable from siblings like create_webhook, revoke_webhook, and get_webhook_deliveries without opening any 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 concrete preconditions and limits: 'Requires webhooks scope; at most ten explicit replays per delivery,' plus an explicit negative scope ('Does not rerun the underlying operation or charge it again'). It references get_events and create_webhook as the sources of its inputs, but does not name an alternative tool for cases where replay is the wrong choice, so it stops short of a full when/when-not/alternative treatment.

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