List Messages in Conversation

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

Annotations already declare readOnlyHint=true, idempotentHint=true, and destructiveHint=false, covering safety. The description adds valuable behavioral detail beyond annotations by specifying exactly what is retrieved (message content, sender information, timestamps, attachments) and the return structure (message type, private flag). This provides transparency about the tool's output and side-effect-free nature without contradicting the annotations.

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 well-structured with a clear purpose line, a concise Args section, a Returns section, and an example. Every sentence serves a purpose—no filler or repetition. It is front-loaded with the action and scope, making it easy for an agent to quickly understand what the tool does. The length is appropriate for the amount of detail provided.

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 simple list tool with two parameters and no output schema, the description is highly complete. It explains both parameters, the response fields (message ID, content, type, sender, timestamp, attachments, private flag), and provides a concrete example. While it doesn't mention pagination or error handling, these are not critical for this tool's basic use case, and the description fully equips an agent to invoke 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 100%, so the schema already documents both parameters thoroughly. The description repeats this information in an 'Args' section and adds a usage example, which is helpful but largely redundant. Since the schema carries the heavy lifting, the description adds marginal value beyond schema descriptions, keeping this at the baseline of 3.

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 verb and resource: 'List all messages in a Chatwoot conversation.' It clearly identifies the scope (a single conversation) and the content (messages with sender info, timestamps, attachments). This distinguishes it from sibling tools like chatwoot_list_conversations (lists conversations) and chatwoot_get_conversation (retrieves a conversation's details).

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 clearly states the primary use case: retrieving all messages from a specific conversation. It implies when to use this tool (when you need message-level detail) and implicitly differentiates it from siblings by focusing on messages rather than conversations or creating messages. However, it does not explicitly mention when not to use it or name alternative tools, so it misses the full criteria for a 5.

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