request_recipient_signature

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

No annotations are supplied, so the description carries the full burden and does so: 7-day link validity, that re-calling replaces a pending request, the returned signature.status of 'pending', the recipient.signature.enrolled webhook firing on completion, and the two 400 rejection conditions. This is exactly the kind of out-of-band behavior an agent cannot infer from the schema.

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-loaded with the action, then consequences, then error cases; every sentence informs. The parenthetical describing the signer's verification flow is the only part that could be trimmed without losing agent-relevant information.

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 and no annotations, the description still covers return shape ('Returns the recipient with signature.status pending'), async completion via webhook, retry/idempotency behavior, and failure modes. Nothing an agent needs in order to call this correctly is missing.

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?

Only one parameter with 100% schema description coverage, so the schema already defines recipientId. The description adds useful preconditions on that value — the recipient must exist in storage and have an email — but does not add formatting or lookup detail beyond that.

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?

Opens with a specific verb and resource: 'email a stored recipient a link to store a reusable signature', and qualifies it as 'Automatic signing'. It also distinguishes the related operation by naming remove_recipient_signature as the prerequisite when a signature already exists.

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 a clear precondition context (recipient must be stored and have an email, must not already have an active stored signature) and routes the agent to remove_recipient_signature in that case. It doesn't explicitly frame when to prefer this over, say, sending an envelope, but the automatic-signing enrolment scenario is unambiguous.

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