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

Adds substantial context beyond the annotations: it discloses that an existing file in that slot is replaced (matching destructiveHint=true), that page 1 and 2 previews are generated, that Printdash file checks run and their notices are returned but never block an order, and that a signed-in account is required with a specific unauthenticated behavior. That is exactly the kind of side-effect and auth detail annotations cannot 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?

Two sentences, front-loaded with the prerequisite PUT step, then the effects. Dense but every clause carries information; the parenthetical about design/side and replacement is the only slightly packed section.

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?

Even though an output schema exists, the description still summarizes the return (preview image plus check notices) and clarifies that notices are the same ones checkout shows and are non-blocking. Auth requirements, side effects, and the upstream dependency are all covered, leaving no gap for a destructive single-param mutation.

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% and there is a single parameter whose description already says it is 'the upload_id request_artwork_upload returned.' The prose reinforces the handoff from that tool but adds no new format, constraint, or semantics beyond what the schema states, so baseline 3 applies.

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 ('puts it on the line', 'Attach an uploaded file to a line') and anchors it to the request_artwork_upload flow, which cleanly separates it from siblings attach_artwork_from_url and attach_artwork_inline. An agent can tell which of the three attach tools applies without opening a schema.

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 clear precondition ('After the file has been PUT to request_artwork_upload's upload_url'), which tells the agent both when to call it and which tool must run first. It never names the alternative attach tools or states when-not to use it, so it stops short of full routing guidance.

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