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

Annotations already indicate destructive and non-idempotent behavior. The description adds that resend may consume notification credits and warns against redundant reminders, providing useful side-effect context beyond the annotations.

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?

The description is concise, front-loads the purpose, and breaks down each action without redundancy. Every sentence adds value.

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?

Given the complexity of two actions and the lack of an output schema, the description covers prerequisites, side effects, and a usage caution. It does not describe return values, but the invocation requirements are well specified.

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 descriptions cover all parameters (100%). The description reinforces the meaning of action values and reminds to use IDs returned from find_documents, adding context beyond the schema's field-level descriptions.

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 clearly states it follows up on an existing assignment and enumerates two specific actions (resend, set_expiration) with their effects, distinguishing it from sibling tools like find_documents or request_signatures.

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 explicitly instructs to use this after checking find_documents and warns against repeating reminders unnecessarily, providing a clear sequence and a caution. However, it doesn't explicitly state when not to use it relative to other follow-up or signing tools.

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