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

With no annotations, the description carries the full burden and does well: it discloses the 5-minute URL expiry, the 100 MB cap, supported formats, and the side benefit that bytes never enter the agent's context. It omits auth/credential requirements for the PUT and what happens if the URL expires mid-upload, which are real gaps for a write-flow tool.

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?

Front-loaded with the return value and the primary workflow, and each sentence adds routing or constraint information rather than restating the name. It is dense and long-ish for a single paragraph, but no sentence is filler.

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?

An output schema exists, so return structure needn't be explained; the description instead covers the full multi-step flow (request URL, PUT, then `process_uploaded_document` with `upload_id`), limits, and format support. An agent has everything needed to execute the flow correctly.

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 ~80%, so the schema already documents `purpose`, `filename`, `size_bytes` and `content_type`. The description adds the supported-extension list, which helps validate `filename`/`content_type`, but says nothing about the optional `authorization` parameter or enum semantics beyond what the schema states. Baseline 3 is right.

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 with scope: returns a short-lived (5-minute) PUT URL plus a ready-to-run `curl_example`. It is immediately distinguishable from `request_download_url` (direction) and the `upload_*_base64` siblings (inline bytes vs. direct PUT).

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?

Explicit routing: shell-access agents run the `curl_example`, non-shell clients surface the URL/command, files under 100KB should use `upload_document_base64`, and the follow-up call to `process_uploaded_document` is named. When-to-use and named alternatives are all present.

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