retry_webhook_delivery

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

Annotations only say readOnlyHint=false and destructiveHint=false; the description adds the key behavioral fact that the original delivery is not mutated but a new attempt is created with the same payload. It also discloses a hard auth prerequisite (PROOF_API_KEY, server restart) and explicitly rules out start_login as a workaround, which prevents a common wrong turn.

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?

The core behavior is front-loaded in the first sentence and the second sentence explains the effect on the endpoint. The separate ACCESS block is clearly sectioned and earns its space by blocking a predictable failure mode, though it could be tighter.

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?

An output schema exists so return values need not be described, and the description covers the auth requirement and retry semantics well. Gaps remain around edge cases an agent would likely hit: what happens if the endpoint was deleted or disabled, and whether repeated retries are allowed.

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?

The single parameter has 100% schema coverage with its own description ("Webhook delivery ID to retry"), so the schema already does the work. The tool description adds nothing about where that ID comes from (list_webhook_deliveries) or its format, so the 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 and resource ("Retry a failed webhook delivery") plus the mechanism ("Creates a new delivery attempt with the same payload to the configured endpoint"), which cleanly separates it from list_webhook_deliveries and get_webhook_delivery. It stops short of naming a sibling explicitly, so it lands just below the top mark.

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?

The word "failed" implies the triggering condition, so usage is inferable, but there is no explicit when-to-use/when-not guidance and no pointer to alternatives such as get_webhook_delivery for first diagnosing the failure. The access note tells the agent to obtain credentials before calling, which is useful but is a prerequisite rather than usage selection guidance.

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