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

With no annotations, the description carries the full burden. It usefully discloses the customer-visible side effect ("The customer sees it on the quote page") and the media-upload prerequisite, but omits permission requirements, idempotency, attachment count/limit behavior, and what happens if the media does not belong to the quote's job.

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 short sentences with no filler, and the core purpose plus the prerequisite are front-loaded. Slight awkwardness in "Show an uploaded photo or file of the same job with a quote" costs a point.

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 three-parameter mutation with no annotations and no output schema, the description covers purpose, prerequisite, and user-visible outcome, but leaves gaps around ownership validation, mutation side effects, and failure modes that an agent would want before calling it.

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 0%, so the description must compensate. It does partially: it identifies the caption as optional, explains that media_id comes from a prior media upload, and implies quote_id is the target quote. It adds no format or constraint detail (e.g., ID shape, caption limit) beyond 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 identifies the resource (a photo/file attached to a quote) and the effect (it becomes visible to the customer on the quote page), which is enough to distinguish it from quotes_listAttachments and quotes_removeAttachment. However, it phrases the action as "Show" rather than "attach," and the phrase "of the same job" is ambiguous about whether media must belong to the quote's job.

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?

It gives a concrete prerequisite and routes the agent to the right preceding step: "Upload it first with the media ops." It does not state when not to use this tool or explicitly name alternatives, but the context for use is clear.

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