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

With no annotations, the description carries the full burden and does so well: it discloses one-time use, allowed file types, plan-specific size caps, the authoritative `max_bytes` field, 15-minute expiry, and editor role requirement. It also explains the returned `curl` command and JSON response containing `url`.

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?

The description is dense but front-loaded: it opens with the core purpose, then explains mechanics, limits, expiry, and alternatives. Every sentence provides actionable information for correct invocation.

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 no output schema and no annotations, the description still covers the essential return behavior (`curl` command, JSON response with `url`, `max_bytes`), operational constraints, role requirement, and next step. Nothing critical for correct selection and invocation is missing.

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 the schema already documents `slug`, `filename`, and `content_type` thoroughly. The description adds process context but does not add meaning beyond the schema for these parameters, so baseline 3 is appropriate.

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: get a one-time upload link for a local file into Dock. It clearly distinguishes itself from `create_video_upload` for video surfaces and from `upload_file`, which is the next step after obtaining the link.

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?

Explicitly says when to use it (file on your machine, PDF/image/spreadsheet/audio/archive, over ~3 MB, no public host), when to use an alternative (`create_video_upload` for video surfaces), and how to sequence it with `upload_file`.

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