check_permissions

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

With no annotations provided, the description carries the full burden of behavioral disclosure. It effectively describes the tool's behavior by specifying what it checks (permissions for specific paths) and what it returns (a dictionary with access status, paths checked, error messages, and macOS version). However, it lacks details on potential side effects, error handling, or performance characteristics like execution time.

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 well-structured and front-loaded with the main purpose in the first sentence, followed by bullet points for clarity and a returns section. Every sentence adds value without redundancy, making it efficient and easy to parse.

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 the tool's complexity (simple permission check with no parameters), the presence of an output schema (which handles return values), and the detailed description covering purpose, usage, and behavior, the description is complete enough. It provides all necessary context for an AI agent to understand and invoke the tool correctly.

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 tool has 0 parameters, and the schema description coverage is 100%, so no parameter documentation is needed. The description does not add parameter-specific information, but this is appropriate given the lack of inputs. A baseline of 4 is assigned as it compensates adequately for the zero-parameter case.

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 with specific verbs ('check if the server has the required permissions') and resources ('iMessage data', 'Full Disk Access for ~/Library/Messages/chat.db', 'Access to ~/Library/Messages/Attachments'). It distinguishes itself from sibling tools (e.g., get_conversation_messages, send_message) by focusing on permission debugging rather than data retrieval or message operations.

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 clear context for when to use this tool ('helps debug permission issues'), but it does not explicitly state when not to use it or name specific alternatives among the sibling tools. It implies usage for troubleshooting access problems without detailing prerequisites or exclusions.

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