search_messages

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

With no annotations provided, the description must disclose behavior itself, and it does reveal two non-obvious traits: results are sorted newest first and matching is literal substring rather than regex/fuzzy. However, it omits other behavioral details such as pagination, case sensitivity, and what happens with large result sets.

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?

Two short sentences, no filler, with the most important behavioral facts (resource, ordering, matching mode) front-loaded. Every word contributes.

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 five-parameter tool with no output schema and no annotations, the definition is incomplete. It does not explain the time/position parameters, result shape, or pagination, so an agent has to guess at valid usage for all optional parameters.

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%, and the description only clarifies the query parameter semantics ('matches a literal substring'). The after, before, limit, and chat_id parameters are left to name inference, with no date format, default behavior, or interaction explained.

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 action (Search) and resource (message text), and adds distinguishing detail: newest-first ordering and literal substring matching. This separates it from sibling tools like list_messages, which would not perform text search.

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 makes the intended use case clear — retrieving messages by a literal text substring — but it does not explicitly contrast this with list_messages or list_chats or state when not to use it. No misleading guidance is present.

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