upload_file_v2

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

No annotations are provided, so the description carries the full burden of disclosing behavioral traits. It fails to mention important details such as whether the file is overwritten or appended on conflict, size limits, authentication requirements, or any side effects. For a mutation tool, this is insufficient transparency.

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 extremely concise: two sentences that front-load the core action and parameters. Every word is necessary and informative. There is no fluff or repetition, making it easy for an AI agent to quickly understand the tool's purpose.

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, no annotations, and no output schema, the description is too minimal. It does not clarify what the return value looks like, potential error conditions, or any constraints like file size limits. A user-scoped file upload tool should provide more context about the operation's implications.

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?

The input schema covers 100% of parameters with descriptions, so the baseline is 3. The description reiterates the key parameters (base64 file content, filename) and mentions optional flags (append, ephemeral) but does not add meaningful semantic information beyond what the schema already provides. It meets the minimum bar but does not enhance 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 identifies the action (upload), resource (user-scoped file), and the specific API endpoint (/api/v2/files). It also distinguishes from other upload tools (e.g., upload_file, upload_project) by specifying 'user-scoped', which implies per-user files. This leaves 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 implies the tool is for user-scoped files, which provides some context compared to other upload tools, but it does not explicitly state when to use this tool versus alternatives (e.g., upload_file v1), nor does it mention any preconditions or when not to use it. The guidance is implicit and minimal.

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