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

Beyond annotations it adds the auth prerequisite ("Requires an account connection"), the storage semantics (original files kept, no parsing), the request_id retry convention, and a note that the endpoint returns English natural-language text. Annotations already cover readOnly/destructive/openWorld, so this is solid added context; the retry-by-request_id advice sits slightly awkwardly next to idempotentHint=false but is a dedupe-key pattern rather than a contradiction.

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 opening sentence front-loads the purpose well and most sentences carry real information (auth, scope limits, next step). The closing line about a "public endpoint" returning "English natural-language text, preserving sources, conditions and pagination" reads as boilerplate and is actively confusing for a tool that stores files.

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?

The tool is a write operation with a nested file array, no output schema, and zero schema description coverage, so the description should do more. It covers auth, scope, upstream/downstream workflow and roughly what comes back (ready attachment IDs), but never explains how a file entry is assembled or what makes an attachment "ready".

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 parameter burden, and it only partially does: it explains request_id reuse and the intent constraint on which files to attach. The nested file object (file_id, download_url, file_name, mime_type), the 1-10 item bounds, and the UUID pattern for request_id are left entirely to the raw schema.

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?

"Save user-selected chat files as attachments for feedback" gives a specific verb plus resource, and the negative clause "it does not parse documents or publish news" rules out adjacent interpretations. It also names the downstream sibling (submit_feedback), so an agent can place it in the feedback workflow, though it never contrasts itself with prepare_feedback_upload.

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?

Clear context for use: an account connection is required, only user-intended publication files should be attached, and the returned IDs feed submit_feedback. The main gap is that the closest alternative (prepare_feedback_upload) is never mentioned, so the agent must infer which of the two upload paths to pick.

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