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

No annotations are provided, so the description carries the transparency burden. It discloses the return shape (permission summaries, total_count), the token cost, and the connection targeting behavior. However, it does not explicitly state that this is a read-only operation or describe pagination behavior beyond what the schema already provides.

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 compact and front-loaded with the core purpose in the first sentence. Each subsequent sentence adds essential operational detail (prerequisite call, parameter targeting, return info, cost) with no unnecessary verbiage.

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 rich input schema (all parameters described) and the presence of an output schema, the description covers the key prerequisites and provides a high-level summary of results. The inclusion of the prerequisite get_connected_accounts call and the token cost makes it contextually complete for a list tool.

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 baseline is 3. The description adds meaningful context for clerk_instance_id by explaining its relationship to clerk.get_connected_accounts and the default behavior, exceeding the schema's generic description.

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 states a specific verb+resource: 'List organization permissions in a connected Clerk application.' This clearly distinguishes it from sibling tools like clerk.list_organization_roles and clerk.list_organizations, which deal with different resources.

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?

It provides clear context by instructing to call clerk.get_connected_accounts first and explains how to use clerk_instance_id to target a specific connection or omit it for the default. However, it does not explicitly state when not to use this tool or compare it to alternative list operations.

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