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

Goes well past the annotations, which only mark this as a non-readonly, non-destructive, non-idempotent write. The description discloses the 20-minute expiry of the new quote, that no code is emailed, that no money moves (buyer pays from their own wallet), the no-op answer for orders where crypto isn't offered, and the refusal paths. That is exactly the behavioral context the hints cannot convey.

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?

Front-loads the trigger condition and is dense with useful detail, but the closing sentence about crypto not being offered is a multi-clause edge case that could be tightened. Most sentences earn their place; a couple of qualifiers could be trimmed without loss.

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, the description does a good job covering effects and refusals, and naming the new amount plus window implies what the response carries. It stops short of stating what the result actually returns (new address, amount, expiry) or whether the previous quote's payment address stays valid, which matters for a quoting 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?

The single parameter has 0% schema description coverage, so the description carries the burden, and it only implies the parameter through repeated references to 'an order' and to get_order_status as the source. It never says what order_token is or where to obtain it, though the name makes the intent largely self-evident.

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 ('asks for a new quote') plus the exact outcome (new amount, 20-minute send window) and anchors it to a trigger state from get_order_status. It is clearly distinguishable from start_crypto_payment and from simply resending against an existing quote.

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 an explicit precondition (quote expired before payment arrived, per get_order_status), an explicit alternative for the refusal case ('send against that one'), and three named refusal conditions: still inside the 20 minutes, payment already seen, order no longer awaiting payment. Nothing about when to call is left to inference.

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