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

Annotations already mark the tool read-only, idempotent, and non-destructive. The description adds valuable behavioral context beyond that: results are newest-first, hasMore indicates more items exist, and the tool intentionally does not return download URLs or parsed contents. This exceeds what the annotations or schema alone would convey.

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, all information-dense and front-loaded. The core action and ordering appear first, followed by practical filtering guidance, a pointer to get_file, and pagination behavior. No filler or repetition of schema details.

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 output schema exists, the annotations cover safety, and the schema documents all parameters, the description covers the remaining contextual needs: ordering, pagination semantics, filter-first guidance, and the handoff to get_file. An agent has everything needed to call this correctly.

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 baseline is 3. The description adds meaningful param-level guidance by telling agents to prefer nameContains over pagination and to only use nextPageToken when full enumeration is required. It does not re-describe each field, which is appropriate since the schema already handles that.

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 ('List files in the workspace'), adds ordering semantics ('newest first'), and clarifies scope by referencing the 'files group'. It also distinguishes list_files from the related get_file tool, making its purpose clear without opening schemas.

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 explicit usage direction: prefer nameContains over broad pagination, use get_file for download URLs or parsed contents, and only pass nextPageToken when every item is needed. It also explains hasMore semantics, leaving no ambiguity about when to use this tool versus alternatives.

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