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

Annotations are empty, so the description carries the full burden—and it meets it well: it discloses that the tool only returns a presigned URL (doesn't attach the logo), that the upload is a separate HTTP PUT, that the URL expires, and that set_agent_logo must follow. It doesn't state failure modes or whether upload_url is single-use, but the core behavior is transparent.

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?

Dense but organized: purpose first, then parameters, then the upload workflow with a concrete curl example. The curl example adds length but earns its place by clarifying the exact follow-up step.

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?

With no annotations and no output schema, the description still covers inputs, return values (upload_url, logo_key, expires_in_seconds), the mandatory follow-up set_agent_logo call, size and expiry constraints, and the required HTTP method. An agent can execute the full flow from this text alone.

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 coverage is 100%, so baseline is 3; the description adds value by clarifying where agent comes from (list_agents), which content types are allowed, the 2 MB limit, and how the optional size parameter is used. This goes beyond the schema without duplicating it.

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 and resource: 'Start uploading a logo image' for a team agent, and immediately clarifies the purpose (watermark when logo_watermark_enabled). It clearly distinguishes the create-upload step from the later set_agent_logo attachment step, so an agent knows exactly what this tool does.

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 an explicit workflow: pass agent (from list_agents), filename, and content_type, get a presigned URL, PUT raw bytes without extra headers, then call set_agent_logo. It also states the 2 MB size constraint and that the URL expires, which are key usage constraints. Sibling tool distinction is implicit but sufficient.

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