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

Goes well beyond the annotations (which only state non-read-only, idempotent, non-destructive, open-world) by disclosing that keys are never echoed back, the exact semantics of connected=false and webhookConfigured=false, that payments remain disabled until setup_payments runs, and the instruction never to invent keys. This is exactly the extra behavioral context annotations cannot carry.

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?

Front-loaded with the core action and the critical 'does NOT enable payments' caveat, and every sentence carries operational meaning. It is on the long side, but the density is justified rather than padded.

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?

No output schema exists, so the description correctly explains the return shape ({ connected, webhookConfigured }) and what a false value implies, plus the pre-requisite relationship with setup_payments and get_stripe_status. Nothing an agent needs to invoke this safely is missing.

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 already 100%, so the baseline is 3, but the description adds real meaning: the key value formats, where in the Stripe dashboard to find them, that both are required, and the instruction to ask the user rather than guess. That is genuine value beyond the schema text.

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?

States a specific verb and resource ('Store the app's Stripe API credentials') and names the downstream capability it enables (billing, checkout, subscriptions, portal). It clearly separates itself from setup_payments and get_stripe_status, which is exactly what an agent needs to choose among 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?

Explicit when-to-use and when-not: prefer setup_payments for first-time setup, use this only to rotate keys on an app where payments are already enabled, and use get_stripe_status to inspect state without writing. It also routes the agent to get_integration_guide before writing consuming code.

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