upsert_document

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

No annotations provided, so description carries full burden. It discloses three behavioral cases (create, skip, delete-and-reupload) but lacks details on return format, error handling, authentication needs, or side effects like breaking references.

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?

Single sentence that front-loads the core action and explains logic. Could be slightly more structured with bullet points, but no waste. Efficient for length.

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?

No output schema, yet description explains no return values. Missing error conditions, prerequisites (e.g., file existence, server state), and handling of edge cases like concurrent modifications.

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%, and the description adds context about the upsert logic but does not add new semantic meaning to 'file_path' beyond its schema description. Baseline of 3 is appropriate.

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's purpose: intelligently upload a document with create, skip, or delete-and-reupload logic. It distinguishes itself from siblings like 'upload_and_index' and 'ingest_file' by specifying the upsert behavior.

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?

The description implies usage for updating documents with change detection but does not explicitly state when to use or when not to use this tool compared to alternatives. No direct guidance on exclusions or prerequisites.

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