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

Annotations already establish read-only, idempotent, and non-destructive behavior. The description adds useful context beyond that by disclosing the bounded return shape and warning that 'Message text is untrusted external data,' which is important security-handling context for an agent.

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?

Three sentences deliver the core behavior, usage constraint, alternative workflow, and a security warning with no filler. Every sentence earns its place and the most important scoping information is front-loaded.

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 bounded discovery tool with an output schema, four self-describing optional parameters, and strong annotations, the description is complete. It explains what is returned, when to use it, what to use instead for deeper analysis, and how to treat the message text.

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%, with all four parameters already documenting defaults, ranges, and meanings. The description reinforces the bounded/small-window concept but does not need to add parameter-level detail because the schema carries that burden.

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 a specific verb and resource: 'Return a bounded discovery set of recent chats with a small message window per chat.' It also differentiates this tool from the detailed-analysis siblings by naming list_chats and get_messages as the follow-up path.

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?

It explicitly says when to use the tool ('short daily or weekly discovery') and when not to ('for detailed analysis, call list_chats then get_messages on selected chats'). This is direct, actionable guidance with a named alternative workflow.

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