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

Adds substantial context beyond the destructiveHint=true annotation: the message is really delivered and visible in the visitor's widget, may reach them on a connected channel, cannot be undone from this tool, and has the side effect of creating a new chat. It also explains the conditional idempotency semantics of external_id, which is exactly the nuance the flat idempotentHint=false annotation cannot express.

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 consequence and irreversibility are front-loaded in the first two sentences, followed by the confirmation protocol and the retry mechanism. Every sentence carries operational information; nothing is repeated from the schema or annotations.

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 destructive, open-world send with four required parameters and no output schema, the description covers side effects, irreversibility, and the confirmation gate well. It does not state what a successful call or a deduplicated retry returns (e.g., a message id), which is the one remaining 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, but the description earns extra credit by explaining the confirm gate as a user-approval contract and by defining external_id's idempotency scope (same id + same visitor's latest chat = duplicate). The 5000-character text limit and id sourcing remain schema-only concerns.

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?

Names a specific verb and resource with scope: sends a real outbound message to a website visitor in their Chaport chat as a given operator. It also distinguishes itself behaviorally from the read-oriented siblings by stating that a new chat is started when no recent one exists, so an agent can tell this apart from chaport_get_chat or chaport_update_last_visitor_chat.

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?

Gives an explicit pre-call protocol (confirm text and recipient with the user first, then pass confirm: true) and a retry policy (use external_id for safe retries). It also indirectly routes the agent to chaport_list_visitors and chaport_list_operators via the schema. It stops short of naming a sibling to use instead for adjacent cases, so it is clear context without explicit alternatives.

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