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

Annotations already declare read-only, idempotent, and non-destructive behavior. The description adds behavioral context by mentioning filtering options and the privacy_mode that controls output detail level. It does not contradict annotations and provides useful information about output control, though it could further clarify returnt structure or pagination behavior.

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 concise and well-structured: the first sentence states the core purpose, and the second sentence lists the key filtering capabilities and the privacy_mode feature. It is front-loaded with the primary action and avoids unnecessary detail. Every word contributes to understanding.

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?

The tool has 8 optional parameters with full schema coverage, so the description needs to add contextual clarity beyond the schema. It effectively communicates the purpose and high-level capabilities, and mentions the privacy mode affecting output. However, without an output schema, it does not describe what fields or structure the history entries contain, leaving some ambiguity for the agent. It is adequate but not exhaustive.

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?

The input schema covers 100% of parameter descriptions, so the baseline is 3. The description mentions 'date range, operation type, status, and source' which echoes the schema parameters (since, until, operation, status, source) and 'privacy_mode' is also mentioned. It does not add substantive meaning beyond the schema, so a score of 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: 'View the history of file organization operations.' It uses a specific verb (view) and resource (history), and distinct from all sibling tools that perform operations like organizing, scanning, or deleting. It also hints at filtering capabilities, making the purpose unambiguous.

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 implies usage when you need to see past operations, but it does not explicitly state when to use this tool versus alternatives or mention any exclusions. There is no reference to other tools that might be more appropriate for similar tasks. The filter capabilities provide context, but no direct guidance on selection.

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