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

Beyond the destructiveHint annotation, the description discloses that removal is permanent, that the filing-history row is retained and marked discarded, and that user confirmation via confirm: true is required. This gives the agent meaningful behavioral context for a destructive operation.

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?

Three sentences front-load the core action, then add use cases, the confirmation requirement, and the retention side effect. Every sentence contributes useful information with no filler.

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 two-parameter destructive tool, the description is complete: it explains what is removed, when to use it, what must be provided, and what residual record remains. The schema covers parameter source for upload_id, and no output schema is needed for this operation.

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%, so the schema already documents both upload_id and confirm. The description repeats the confirm requirement but adds no parameter-specific detail beyond what the schema provides, so the baseline 3 is appropriate.

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 states a specific verb and resource: 'Permanently remove a user-selected file from the Caribooks document box.' It also distinguishes itself from related flows by noting it happens 'without attaching it to QuickBooks' and by naming the intended cases: unwanted documents, duplicates, and unrelated files.

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 gives clear context for when to use the tool ('Intended for unwanted documents, duplicates and unrelated files') and the required approval gate ('Requires confirm: true after the user's approval'). It does not explicitly name alternatives or when-not-to-use conditions, so it stops short of a 5.

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