search_messages

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

No annotations are provided, so the description must disclose behavior. It only states that it searches all chats, without detailing performance, pagination, error handling, or what happens with empty queries or limits.

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 very concise, with two sentences and a bullet list. It front-loads the core purpose. However, it could be more structured (e.g., separate sections) to improve readability for complex use cases.

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 (2 parameters, no nested objects) and the presence of an output schema, the description is mostly adequate. However, it lacks usage context and any mention of return structure, leaving some gaps for an agent.

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%, yet the description adds only minimal clarification: 'The text to search for' for query and 'Maximum number of results to return (default 50)' for limit. This adds little beyond the schema's title fields, failing to compensate for the lack of schema descriptions.

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 the tool searches all iMessage chats for messages containing the query text, specifying the verb 'search', resource 'iMessage chats', and scope 'all'. It distinguishes from siblings 'get_messages' (which likely retrieves specific messages) and 'list_chats'.

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?

No guidance is provided on when to use this tool vs. its siblings ('get_messages', 'list_chats'), nor are there any prerequisites or exclusions mentioned. The agent is left to infer usage context without explicit direction.

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