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

With no annotations provided, the description effectively carries the transparency burden. It explicitly states the action is permanent, that the file is removed from storage, and that linked upload sessions are marked expired. It also notes the cost is 0 tokens. This is strong disclosure of side effects and irreversibility, though it doesn't cover error cases or permissions.

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 three short sentences, each adding distinct value: purpose, source of file_name, and side effects/cost. There is no filler or redundancy.

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 destructive tool with an output schema and no annotations, the description covers the essential context: what the tool does, where to get the input, what happens to the file and session, and cost. It omits error handling details, but these are not required for basic use, and the output schema handles return formats.

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?

The input schema has 100% description coverage for the single required parameter, providing the format and source. The tool description reinforces this by telling the agent to pass file_name from files.list_uploaded_files, adding actionable guidance on where to retrieve the value. This exceeds the baseline for fully documented schemas.

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 opens with a specific verb+resource: 'Permanently delete a file from the authenticated account's upload storage.' This clearly distinguishes it from sibling file tools (download, extend, list, move, upload) by its destructive and specific scope.

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 provides clear usage context: it instructs the agent to pass file_name from files.list_uploaded_files, establishing a prerequisite and source for the parameter. It does not explicitly mention alternatives or when-not-to-use, but the purpose is clear enough, so it earns a 4.

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