retry_failed_webhook

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

With no annotations, the description fully discloses multiple behavioral traits: it only marks events for retry (actual re-dispatch is manual), uses deterministic idempotency for duplicate detection, requires approval for actual execution, returns specific shapes, emits audit events, and has access restrictions. This is comprehensive.

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 description is well-structured with the purpose in the first sentence, followed by selection criteria, behavior, and return shapes. It is somewhat verbose but every sentence adds necessary information. Could be more concise, but it is not overly long for the complexity.

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?

Given the tool has no output schema and six parameters, the description provides complete context: input semantics, behavioral nuances (dry run, duplicates, access control), explicit return shapes for both dryRun true/false, audit details, and idempotency. No gaps remain.

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 input schema has 100% parameter description coverage, but the description adds value by explaining how parameters interact (e.g., combining eventIds with fromTimestamp, 7-day cap on range, dryRun behavior, approvalId usage, maxRetries cap). It goes beyond the schema's individual descriptions.

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?

The description explicitly states the tool marks failed Stripe webhook events for reprocessing, with specific verb 'retry' and resource 'failed Stripe webhook events'. It distinguishes itself from sibling tools like test_webhook by noting it is an internal founder-operations-only recovery tool, and focuses on a narrow use case.

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 description clearly states when to use the tool: to retry failed Stripe webhooks, even providing a common prompt phrase. It mentions access restrictions (403 for general accounts) and internal nature, but does not explicitly list alternative tools or scenarios where it should not be used.

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