upload_file

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

With no annotations, the description carries full burden. It reveals the critical Content-Type requirement and rejection behavior. It does not mention file size limits, authentication, or error handling for missing files, but covers the essential API behavior.

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?

Three concise sentences, front-loaded with the main action, then crucial requirements, then token usage. No extraneous information.

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 no annotations, no output schema, and file upload complexity, the description explains the upload process and token purpose well. It lacks details on response structure (e.g., token format) but is adequate for usage.

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 covers 100% of parameters with descriptions. The description adds value by emphasizing the content_type must be 'application/octet-stream' and explaining the token's role in later operations, going beyond schema details.

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 'Uploads a binary file to Redmine and returns an upload token.' It specifies the verb and resource, and distinguishes from sibling tools like create_project_file by explaining the token-based workflow.

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 explicitly instructs to always set Content-Type to 'application/octet-stream', warns of HTTP 406 rejection, and explains token usage for subsequent operations. It does not explicitly list when not to use this tool, but context from siblings implies this is for initial token generation.

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