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

Beyond the annotations (readOnlyHint=false, openWorldHint=true, destructiveHint=false), the description adds substantial operational detail: token lifetime ('short-lived'), hard limits (10 files, 20 MiB per file, 50 MiB combined per feedback including later additions), the required X-Upload-Token header, and security guidance ('never log upload tokens'). 'Reuse request_id for retries' is in mild tension with idempotentHint=false but reads as retry-key deduplication rather than a contradiction, so no flag is warranted.

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 content is dense and front-loaded: capability, prerequisites, return payload, then the follow-up step and limits. The closing sentence about returning 'English natural-language text, preserving sources, conditions and pagination' is generic boilerplate that does not map to this tool's actual behavior and could be cut without loss.

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 two-step upload handshake with no output schema, the description supplies the missing return contract (upload_url, X-Upload-Token, curl example, ready IDs) and the constraints an agent must respect, so it is callable without guessing. The only gap is that 'short-lived' is never quantified, so an agent doesn't know how quickly the PUT must follow.

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 description coverage is 0%, so the description must carry the semantics, and it does for most of it: it explains that files are per-attachment items with a count ceiling and per-file byte ceiling, and it gives request_id a purpose as the key to reuse on retries. It does not explain file_name (extension/display-name conventions) or that request_id must be a 36-character UUID, leaving the remaining gap to the schema constraints.

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 first sentence states a specific verb and resource ('Prepare a short-lived, single-file upload capability') scoped to 'each local feedback attachment', which cleanly separates it from sibling write tools like submit_feedback and import_feedback_attachments. It also says what the agent gets back (text instructions, curl example, JSON upload parameters), so the tool's role in the flow is unambiguous.

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 a clear flow ('Upload original bytes directly to the returned CRM upload_url with X-Upload-Token, then use ready IDs with submit_feedback') plus prerequisites (account connection, client-side local file and HTTP PUT access) and exclusions ('Do not put bytes or Base64 in MCP arguments'). It never explicitly contrasts itself with the sibling import_feedback_attachments, which is the most likely alternative an agent would consider, so routing is implied rather than fully spelled out.

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