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

Annotations already declare this as a safe read operation (readOnlyHint=true, destructiveHint=false). The description adds useful non-annotation context: the exact fields returned, the PDF-as-one-item expansion behavior, and the duplicate-creation warning. It does not cover pagination defaults, but the added behavioral detail is substantial.

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-loaded with purpose and output summary. The parenthetical about PDF expansion is dense but valuable, and all sentences earn their place. Minor length but no wasted prose.

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 list tool with four optional params and no output schema, the description compensates by naming the returned fields and giving usage guidance. Annotations cover the safety profile. It is complete enough for correct invocation, with only pagination behavior left implicit.

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 fully documents all four optional parameters. The description reinforces the search-before-upload guidance but adds no new syntax or meaning beyond what the schema provides.

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?

States a specific verb and resource: 'List media files in the workspace,' and enumerates the returned fields. It does not explicitly contrast with sibling list tools like list_folders or list_posts, but the 'media files' resource is distinct enough to be clear.

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?

Gives a concrete when-to-use: search here before uploading to avoid duplicates. Also points to create_folder / list_folders for organizing assets. It lacks explicit exclusions or comparison to other list tools, but the context is clear.

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