send_file

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

Annotations already indicate destructiveHint=true. The description adds 'Delivered immediately, no undo', providing behavioral context beyond annotations (immediate delivery, irreversibility). This aligns with the destructive hint and adds useful nuance, though details like file size limits are omitted.

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 sentences, front-loaded with the core action, and no superfluous words. Every sentence adds value: purpose first, then behavioral impact. Structure is optimal for quick comprehension.

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's simplicity (3 params, no output schema), the description covers essential aspects: action, resource, delivery, and irreversibility. It does not mention file size limits or supported types, but for a basic upload tool, it provides sufficient context for an agent to use it 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?

Schema description coverage is 67% (2 of 3 parameters described). The description does not add parameter meaning beyond schema: 'chat' is well-described in schema, 'path' minimally, 'caption' has no description. Baseline at 3 is appropriate; no compensation from description for the missing caption parameter.

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 'Upload a local file to a chat', specifying the verb upload and resource local file. It distinguishes from sibling tools like send_message or download_media, though no explicit differentiation is provided. The purpose is clear and actionable.

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 uploading local files to chats but lacks explicit guidance on when to use versus alternatives (e.g., send_message for text or remote media). No when-not-to-use or prerequisite conditions are stated, leaving the agent to infer context.

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