Upload file

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

Beyond the annotations, the description discloses that larger local files are automatically streamed via an upload session, which is non-obvious and useful. It does not contradict the readOnly/idempotency hints and does not need to restate the write side effect already implied by readOnlyHint=false.

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 two tight sentences that lead with the primary purpose and then pack the two most important behavioral details. No filler or repetition of schema descriptions.

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?

For a 5-parameter upload tool with no output schema, the description plus schema covers the essential input modes, conflict behavior via mode, and large-file handling. It could mention return behavior or parent-folder creation, but these are not blocking for an agent to call the tool correctly.

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 80% schema coverage, the schema already documents most parameters; the description adds the crucial 'either text or localPath' relationship and the automatic chunking threshold, which are not encoded in the schema. It leaves autorename underexplained, but that parameter also lacks an in-schema description, and the added context is valuable.

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 'Upload content to a path', a specific verb and resource, and clearly distinguishes the tool from read/list/delete siblings by its write intent. It also clarifies the two input forms (text or localPath), leaving no ambiguity about what the tool does.

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 gives clear direction on when to choose inline text versus a local file and explains the ~140 MB threshold for single vs. chunked uploads. It does not explicitly name alternative sibling tools or state when not to use upload, but no other sibling performs uploads, so the guidance is sufficient.

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