upload_document

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

No annotations are provided, so the description carries the full burden. It mentions the requirement to attach to exactly one entity and the classification flags, but fails to disclose important behaviors such as whether the upload overwrites existing documents, required permissions, size limits, or the response format (e.g., does it return a document ID?). This is a significant gap for a mutation tool.

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 concise and well-structured, with clear sections for the doc format and flag explanations. It is front-loaded with the main purpose and entity constraint. Minor improvement could be more bullet-like formatting, but overall effective.

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 9 parameters, no output schema, and moderate complexity, the description covers the essential: doc format, entity attachment, and flag meanings. However, it lacks details on error handling, success response, and what happens if multiple entity IDs are provided (though implied exactly one). It is adequate but not fully complete.

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?

With 100% schema coverage, baseline is 3. The description adds substantial value beyond the schema: it explains the doc field must be a base64 data URI with examples, clarifies that exactly one entity ID should be provided, and describes the meaning of each boolean flag in natural language. This improves understanding.

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 action ('Upload a document'), the target ('to a property, project, or contact'), and the platform ('Propstack'). It also distinguishes from sibling tools as the only upload-specific tool, and specifies the classification flags. No ambiguity.

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 when to use (when uploading a document) but does not explicitly compare with alternatives like list_documents or other create tools. No 'when not to use' guidance is provided. The context from sibling names helps but is not explicit.

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