Longhand

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

No annotations are provided, so the description carries the full burden. It discloses key behavioral traits: returns matches with surrounding context (N events before/after), efficiency compared to manual pagination, and semantic matching. However, it lacks details on permissions, rate limits, error handling, or output format, which are important for a search tool with no 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 front-loaded with the core purpose in the first sentence, followed by usage guidance and efficiency comparison. Every sentence adds value: the second clarifies when to use it, the third explains the return format, and the fourth contrasts with alternatives. No wasted words.

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 no annotations and no output schema, the description does well by explaining the tool's behavior, usage context, and efficiency. However, it lacks details on output format (e.g., structure of returned matches) and error cases, which are important for a tool with 6 parameters and no structured output documentation.

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 all parameters. The description adds minimal value beyond the schema: it implies 'session_id' and 'query' are required (though the schema states this) and hints at 'context_events' functionality. No additional syntax or format details are provided, so the baseline 3 is appropriate.

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's purpose: 'Search within a specific session and return matches WITH surrounding conversation context.' It specifies the verb ('search'), resource ('session'), and scope ('with surrounding context'), and distinguishes it from sibling tools like 'search' (general) and 'get_session_timeline' (manual pagination).

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 explicitly states when to use this tool: 'when you know WHICH session to look in but need to FIND a specific discussion or event.' It also provides clear alternatives: 'Much more efficient than paginating get_session_timeline manually,' naming a specific sibling tool and explaining why this tool is preferable in this context.

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