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

No annotations are provided, so the description carries the full burden of behavioral disclosure. It does disclose the prerequisite (get_connected_accounts), the ability to target a connection, and the return value ('Returns the updated permission summary'). However, it does not explain partial update semantics (e.g., which fields are actually updated when omitted) or any potential side effects beyond 'update,' leaving some behavioral ambiguity.

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 four sentences with no redundancy. It front-loads the core purpose, then gives necessary prerequisite and targeting instructions, mentions the return value, and notes the token cost. Every sentence earns its place, making it both concise and well-structured.

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 low complexity (4 params, 1 required) and the presence of an output schema, the description covers the essential workflow: prerequisite, connection targeting, and return value. It does not address error cases or validation, but the existing schema and output schema fill in the gaps, making this reasonably complete for its 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 description coverage is 100%, so the schema itself fully documents all four parameters. The description adds marginal value by restating the clerk_instance_id behavior, but it does not enrich the meaning of permission_id, name, or description beyond what the schema already provides. This aligns with the baseline of 3 when the schema handles parameter semantics.

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 begins with 'Update an organization permission in a connected Clerk application,' which is a specific verb+resource statement that clearly distinguishes this from sibling tools like create_organization_permission, delete_organization_permission, and list_organization_permissions. It also mentions the return value, further clarifying the tool's purpose.

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 operational guidance: 'Call clerk.get_connected_accounts first' and 'Pass clerk_instance_id to target a specific connection, or omit it to use the default account.' This provides clear context for how to invoke the tool correctly, though it does not explicitly contrast with when to use alternative tools (e.g., create vs update), making it a 4 rather than a 5.

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