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

Beyond the annotations (which only say non-read-only, open-world, non-destructive), the description discloses that keys are never echoed back, that re-running replaces the webhook endpoint, what stripeSetupStatus='failed' and webhookConfigured=false mean, and why subscription events may not reach Bridge. This is rich behavioral context the annotations cannot convey.

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?

It is dense and long, but the core action is front-loaded and each subsequent sentence (arguments, key-safety warning, plan alternative, status semantics, follow-up guide) carries distinct information. The density is warranted by the task, though it could be trimmed marginally.

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?

Despite no output schema, the description explains the return signals (stripeSetupStatus, stripeSetupError, webhookConfigured), the credential sourcing and safety requirements, and the required follow-up. An agent has everything needed to call and interpret this 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?

Schema coverage is 100% so the baseline is 3, but the description adds meaning beyond the schema: it gives concrete key formats, points to the Stripe dashboard location, and adds a strong operational directive ('ASK THE USER FOR THESE — never invent, guess, or reuse a key'). That operational guidance exceeds what the field descriptions provide.

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 action and resource ('Connect Stripe to the Bridge app in one step: stores the Stripe API credentials AND turns payments on') and clearly names what it does not do ('does NOT create any plans'), routing to create_plan/set_plan_price/list_plans. This makes it trivially distinguishable from connect_stripe and the plan-management siblings.

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 explicitly states when to prefer this over connect_stripe ('when setting billing up from scratch'), what to use instead for plans, and adds a follow-up step ('call get_integration_guide with topic=billing') before writing consuming code. When-to-use, when-not, and alternatives are all present.

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