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

With no annotations, the description carries the full burden and does so well: it discloses billing behavior (organization balance charged per send/resend), test-mode exemptions (no charge, emails rerouted to the organization), resend side effects (only unsigned signers re-emailed, existing signatures preserved), and a hard precondition (expired contracts cannot be sent). This is exactly the mutation-level context an agent needs.

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?

Four sentences, each carrying distinct operational value, with the primary action and cost model front-loaded. Dense but not padded; no sentence is redundant.

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?

For a single-parameter mutation with no annotations and no output schema, the description covers preconditions, side effects, and billing adequately. It omits return shape and idempotency/double-charge guidance, which output schema absence makes less critical but still a minor gap.

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?

One parameter (contract_id) with 0% schema description coverage, but the schema supplies a format pattern and the name is self-explanatory. The description implies the ID may reference either a draft or a sent contract, adding a little semantics, but no format or sourcing guidance beyond the schema.

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+resource (send/resend a contract) and covers both operating modes — draft vs. already-sent — up front. It does not explicitly name a sibling or contrast itself with contract_update/contract_cancel, so it falls just short of a 5.

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 clear conditions for use: valid on draft or already-sent contracts, invalid past the expiration date, and the resend path is scoped to unsigned signers. No explicit alternatives are named for related actions, but the trigger conditions are unambiguous.

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