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

The description discloses that OnceAsk searches contacts and connected Google/Gmail-derived people, emails the request when possible, and hides the recipient's email/street address from the agent. This adds meaningful behavioral context beyond the annotations, revealing both side effects and privacy boundaries.

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 concise sentences front-load the key trigger ('After the user explicitly confirms') and then cover input modes, behavior, and privacy. Every clause adds information; there is no filler or redundant repetition of the schema.

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 description adequately covers the tool's purpose, prerequisites, input options, side effects, and privacy guarantees. It does not describe the return value or failure behavior, but given the absence of an output schema and the nature of the tool, this is a minor gap rather than a blocking omission.

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%, so the baseline is 3, but the description adds valuable cross-references: it maps query to 'person's name/email when recipientId is not known' and contactId to 'recipientId from resolve_delivery'. This clarifies when to use each parameter beyond the schema's standalone wording.

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 ('request a current delivery address/permission') and the resource (OnceAsk), and clarifies it accepts either a recipientId or a name/email. It clearly differs from siblings like send_handwritten_card and resolve_delivery by focusing on the permission-gathering step.

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 states an explicit precondition ('After the user explicitly confirms they want the recipient contacted') and explains the two accepted input paths. It does not explicitly contrast with send_handwritten_card, but the workflow position is clear enough that an agent knows when to call this rather than the sibling send tool.

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