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

The description adds substantial behavioral context beyond the minimal annotations: async indexing, eventual queryability, base64 payloads, 50MB per-file limit, auth requirements, and a compact error-code map. This is exactly the kind of operational detail an agent needs and annotations do not provide.

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?

Every sentence earns its place: purpose first, then async behavior and limits, prerequisites, auth, errors, and related tools. The layout is dense but highly scannable and free of 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?

The description covers document types, count, limits, async behavior, requirements, auth modes, errors, and related tools. The main gap is not describing the response/job status for the async upload or the exact accepted MIME list, though those are not strictly required for correct invocation.

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 100%, so the baseline is 3. The description echoes some schema content (base64, 50MB max, 1–5 files, `appId` mode behavior) but adds little new parameter-level meaning beyond error codes and the async outcome.

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 opens with a specific verb and resource: uploading documents into an app's RAG sources. It further distinguishes the tool as the app-token/B2B variant of the v1 upload and implicitly separates it from list/delete siblings by naming them as related but different operations.

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 clear prerequisites (selected app or explicit `appId`), auth mode conditions, and error codes, plus names related list/delete tools. It does not explicitly state when to avoid this tool or choose the v1 sibling, but the context is strong enough for an agent to decide correctly.

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