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

Adds real context beyond the annotations: it discloses the required scope (bookings:write) and, crucially, that the first invocation is a validation pass that changes nothing, which explains why a non-readOnly, non-idempotent tool is safe to call speculatively. It does not say what happens if the same file is converted twice or whether existing content is replaced.

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-loads the purpose, then the permission, then the two-call protocol in four compact sentences with essentially no filler. The parenthetical about unknown fields being refused by name is slightly awkward but still earns its place by signaling strict validation.

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?

There is no output schema, and the description only covers the first call's return (summary + confirm_token) — it never says where the editable text lands or what the second call returns. For a multi-step conversion tool with an undeclared output shape, that is a meaningful omission.

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 only 33%, so the description should be carrying more weight. It clarifies confirm_token's two-call lifecycle (though the schema already states this), but leaves file_id and proposal_id completely unexplained — notably why a PDF conversion requires a proposal_id.

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 concrete verb+resource transformation: take an uploaded PDF and produce editable text. That is clearly distinct from sibling document tools like add_document, edit_document and import_file, though the description never names a sibling to reinforce the distinction.

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 strong procedural rule: two calls, the first is non-committal and returns a summary plus confirm_token, the summary must be shown to the person, and the second call repeats the same arguments plus the token. It does not say when to prefer this over edit_document or import_file, which is the remaining gap.

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