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

Annotations already declare readOnlyHint, idempotentHint, and destructiveHint, so the safety profile is clear. The description adds valuable behavioral context by specifying that the search matches against 'section answers and action items', which goes beyond the schema and clarifies the search's scope and semantics. It does not mention pagination or result ordering, but the output schema likely covers return format, and the bar is lower given annotation coverage.

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 three sentences, each earning its place: first defines the action, second gives the use case, third provides sibling alternatives. No redundant or vague wording. It is front-loaded with the primary purpose and is highly scannable.

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 simple search tool with comprehensive annotations, full schema coverage, and an output schema present, the description covers all necessary context: purpose, use case, and alternatives. It doesn't need to explain return values because the output schema exists. The description is complete for the tool's complexity.

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 coverage is 100% with clear descriptions for both 'query' and 'limit'. The description reinforces that query is free-text and matched against content, but it doesn't add significant new meaning beyond the schema. Baseline of 3 is appropriate when the schema carries the parameter documentation.

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 function: 'Search application guides by free-text query' with specific scope ('matched against section answers and action items'). It also distinguishes from siblings by explicitly naming alternatives (guides.get, guides.list), providing clear differentiation.

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 gives explicit guidance on when to use this tool ('Use this when the user describes an engineering challenge... and wants matching guides') and when to prefer alternatives ('Prefer guides.get when you already have the guide slug; prefer guides.list when you need the full inventory'). This satisfies both when-to-use and when-not-to-use criteria.

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