search_conversations

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

With no annotations provided, the description carries full burden but only vaguely mentions 'smart insights' without explaining what these entail (e.g., ranking, relevance scoring, or AI-enhanced filtering). It doesn't disclose behavioral traits like pagination, rate limits, authentication needs, or what 'search' means operationally (e.g., full-text, metadata). This leaves significant gaps for a search tool.

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 a single, efficient sentence that front-loads the core purpose. However, 'smart insights' is vague and could be more precise. It avoids redundancy but misses opportunities to add critical context, making it slightly under-specified rather than optimally concise.

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 search tool with 5 parameters, no annotations, and no output schema, the description is incomplete. It doesn't explain return values, error handling, or the 'smart insights' feature, leaving the agent unsure of behavioral outcomes. Given the complexity and lack of structured data, more detail is needed to guide effective tool use.

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 fully documents all 5 parameters. The description adds no parameter-specific information beyond what's in the schema, not explaining how 'query' interacts with 'smart insights' or clarifying parameter interdependencies. Baseline 3 is appropriate as the schema does the heavy lifting, but the description doesn't compensate with additional context.

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 through 'Claude Code conversation history with smart insights', specifying both the verb (search) and resource (conversation history). It distinguishes from siblings like 'list_recent_sessions' (which lists rather than searches) and 'find_similar_queries' (which focuses on queries rather than conversations). However, it doesn't explicitly mention what 'smart insights' entail, leaving some ambiguity.

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 provides no guidance on when to use this tool versus alternatives like 'list_recent_sessions' for recent conversations without search, 'find_similar_queries' for query analysis, or 'search_plans' for different content. It mentions 'smart insights' but doesn't clarify what contexts benefit from them versus basic search, offering no explicit when/when-not instructions.

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