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

Annotations only say readOnlyHint=false / idempotentHint=false / destructiveHint=false; the description adds substantial behavioral context beyond that: ~25s wait per call, support's 1-3 minute latency, status values, what support can actually do, and the constraint to get user consent before acting on anything that changes files, settings, accounts, or money.

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?

Long but front-loaded and dense with functional instruction: purpose, precondition, parameter sourcing, then call mechanics, then the status-driven loop, then safety and the `readAlongUrl` handoff. No sentence is decorative.

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?

An output schema exists, yet the description still explains the two return fields (`after`, `status`) an agent must act on, plus timing expectations and safety guardrails. For a stateful, multi-call chat tool this leaves no material gap.

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 coverage is 100%, so baseline is 3. The description goes slightly further by framing usage in flow terms: pass the `reportId` returned by `report`, put a hello in the first `message`, and pass `after` with no message to poll — reinforcing how each parameter is used in the conversation loop.

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?

Specific verb+resource: 'Chat live with a Bowmark support agent about a problem you reported.' It ties itself to the `report` sibling and its `reportId`, so an agent can distinguish it from `run`, `run_view`, and the connection tools 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?

Explicit gating ('only after your user said yes to talking to support') plus a full decision loop: call again with `after` and no message when `status` is `waiting`; reply with `message` when `status` is `answered`. Alternatives and conditions are both spelled out.

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