send_files

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

The annotations only indicate read/write, open-world, non-idempotent, and non-destructive behavior; the description adds substantial operational detail: album groups split into ten, mixed-media handling, caption/provenance carried once with later groups replying to the first, the 1024-visible-char limit, allowed_roots path restriction, and the explicit warning not to retry unconfirmed files. This greatly exceeds what annotations provide.

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 dense but every sentence contributes a distinct behavioral or usage constraint. The core purpose and sibling alternative are front-loaded, and the rest consists of necessary boundary conditions rather than filler.

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 complex 11-parameter tool with no output schema, the description supplies most operational context: size limits, mode semantics, media rules, provenance behavior, path restrictions, and retry policy. It is not fully complete because several parameter meanings are absent and the return shape is not described, though the status list 'complete, sent, unconfirmed, not_attempted' gives some expected outcomes.

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 0%, so the description must compensate. It does clarify kind ('use kind=document for a mixed pack'), mode (album vs separate), caption (1024 visible characters), and paths (must be inside files.allowed_roots). However, required parameters agent, model, project, and subject, plus route, format, and reply_to, receive no semantic explanation, leaving clear gaps.

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 a specific action: 'Send explicitly requested files as an album pack... or separate ordered messages,' including precise count ranges. It also distinguishes the tool from send_batch by naming exactly what send_batch is for, so an agent can tell them apart immediately.

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 an explicit when-to-use rule: 'Use this only for a simple signed pack; use send_batch when files need multiple captions, roles/tags, clean client copy or a separate provenance reply.' It also provides media-type guidance with 'use kind=document for a mixed pack,' making usage conditions clear.

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