upload_document

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

With no annotations, the description must carry full burden. It only states the three steps (copy, register, parse) but fails to disclose behavioral traits like whether the source file is modified, whether registration requires authentication, or if parsing is synchronous. No side effects or permissions are mentioned.

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 description is a single 10-word sentence, concise to a fault. It sacrifices necessary detail for brevity. While front-loaded and efficient, it could be restructured with bullet points or additional sentences without losing conciseness.

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?

Given the tool has 4 parameters (with no schema descriptions), an output schema, and many siblings, the description is insufficient. It does not explain parameter behaviors, return value, error conditions, or integration with other tools like register_document.

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%, and the description adds no parameter details. The meaning of source_path (file path on server?), filename (why null?), reparse (what exactly is re-parsed?), and token (authentication token?) are left entirely to inference from names.

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 clearly states the tool copies a server-visible file, registers it, and parses it. The verb-resource combination is specific and distinct from siblings like register_document (which omits the copy step) and reparse_document (which only re-parses).

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?

No guidance on when to use this tool versus alternatives. For instance, when to use register_document directly vs upload_document is not addressed. Prerequisites such as file accessibility or permissions are omitted.

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