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

Annotations already declare destructiveHint=true and idempotentHint=true. The description adds a meaningful precondition: deletion is not permitted when the file is attached to a document in created or awaiting_signatures status. This goes beyond the structured hints and helps an agent predict failure conditions.

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 tight sentences front-load the operation and immediately state the critical constraint. No filler or redundant restatement 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?

For a simple single-parameter deletion tool, the description plus annotations cover destructiveness, idempotencyholmes? wait annotations include idempotentHint true, destructive true. It includes the only important precondition. It doesn't specify permanence or failure behavior, but the schema/annotations carry the rest. Minor gap around what happens if the condition is violated.

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 description coverage is 100%; fileId is described in the schema. The description only restates that the file was previously uploaded, adding no deeper semantic detail about the identifier.

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 the operation ('Delete a previously uploaded file') and identifies the resource (file), distinguishing it from sibling document/draft/webhook deletion tools. The status constraint adds specificity without ambiguity.

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?

The description explicitly provides a usage condition: do not delete files attached to active documents, listing the statuses that make a document active. This is clear context for when deletion is disallowed, though it doesn't explicitly name an alternative tool for other resources.

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