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

With annotations covering only the safety profile (readOnlyHint=false, idempotentHint=true, destructiveHint=false), the description supplies the behaviors that matter: the URL is one-time, valid for 15 minutes, has a 100 MB ceiling, and overwrites whatever exists at path. Overwrite semantics, expiry, and size limit are exactly the extra context annotations cannot express.

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?

Four short sentences, front-loaded with the core action and then the mechanics. Every clause carries information — size cap, example path, shell command, expiry, overwrite behavior — with no 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?

For a no-output-schema tool this covers the full round trip: what it returns (a URL), how to use it, and its constraints. It omits whether special permissions are needed and whether the returned URL should be treated as a secret, which would be the final useful details.

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 75%, just under the high-coverage baseline, so the description must carry some load. It does: path is illustrated with a concrete example (raw/deck.pdf) and its significance explained (pages link to files by path). The note, agent, and workspace parameters are left entirely to their schema descriptions.

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 states a specific verb and resource: get a one-time URL for uploading a file. It also bounds what can be uploaded (image, PDF, deck, up to 100 MB) and clarifies the two-step flow. It does not explicitly distinguish itself from siblings like write_page or list_files, so a 4 rather than a 5.

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 concrete operational guidance: obtain the URL, then PUT with a shell command (curl -T FILE URL), and notes the URL is single-use and expires in 15 minutes. It never states when to prefer this tool over alternatives such as write_page for page content, so it stops short of full when/when-not routing.

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