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

No annotations were provided, so the description carries the full disclosure burden. It prominently warns that the returned secret grants machine authentication and should not be logged or exposed, and also notes the 5-token cost, offering meaningful behavioral context beyond the schema.

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 with clear sections: purpose, security warning, usage steps, return value, and cost. All sentences are relevant and earn their place, though it could be slightly more concise; the organization makes it easily 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 tool with two well-documented parameters, an output schema, and no annotations, the description covers prerequisite calls, connection targeting, sensitivity, return value, and cost. This is sufficient for an agent to select and invoke the tool correctly without needing additional context.

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 reiterates the clerk_instance_id guidance already present in the schema and adds the prerequisite of calling get_connected_accounts, but it provides minimal additional parameter-specific meaning beyond what the schema already conveys.

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 explicitly states 'Retrieve the secret key for a machine in a connected Clerk instance,' using a specific verb and resource. It clearly distinguishes itself from sibling tools like get_machine and rotate_machine_secret_key by focusing solely on secret key retrieval.

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 instructs the agent to call clerk.get_connected_accounts first and explains how to target a specific connection via clerk_instance_id or default to the default account. While it provides clear usage context, it does not explicitly list alternatives or when-not scenarios relative to sibling tools.

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