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

The description discloses that the tool polls Stripe and conditionally settles the payment, which goes beyond the sparse annotations. It does not describe failure handling or repeat-call behavior, but the main side effect is made clear.

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?

Two sentences with zero filler. The mechanism and trigger condition are both front-loaded, and every clause contributes to effective invocation.

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?

The tool has one parameter and an output schema, so most operational detail lives elsewhere. The main missing context is whether this should be repeated until payment appears, which is a minor gap for this tool.

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 coverage is 100% for the single applicationId parameter, and the schema already describes it as a UUID wrapper. The description adds no extra meaning about where the applicationId comes from or how it relates to the pending checkout.

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 names a specific action and resource: re-checks a pending ITIN payment against Stripe and settles it if paid. This clearly distinguishes it from sibling tools like itin_create_itin_checkout and itin_get_itin_application.

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?

It gives an explicit trigger condition: 'Use after the user says they completed checkout.' However, it does not explicitly name alternatives or say what to do when the payment is not yet confirmed.

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