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

Annotations cover the safety profile (readOnly, idempotent, non-destructive), and the description goes well beyond it: it defines what connected=true implies for checkout/subscriptions/billing portal, explains that webhook failures do NOT block checkout but break event sync, clarifies that a single rejection is not a problem versus a sustained streak, and guarantees no key or secret is returned.

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 purpose, then the return shape, then failure semantics and repair path. It is long, but with no output schema the field enumeration earns its place; the dense parenthetical about rejection timing is the only slightly hard-to-parse stretch.

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, and the description compensates fully by enumerating every returned field and interpreting the key ones (webhookConfigured, setupStatus, webhookRejectionsSustained). Failure interpretation and the remediation path are both present, so nothing an agent needs to act on the result 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 description coverage is 100% and the single optional 'app' parameter is already documented there (including the list_apps pointer and the omit-to-use-current behavior). The description adds no further parameter syntax or format detail, so the baseline 3 applies.

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 ('Check whether Stripe is connected to the Bridge app and whether its Stripe webhook works') and distinguishes itself from setup_payments and list_plans by name. An agent can route correctly without opening the schema.

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?

Explicitly says when to call it ('Call this before assuming billing works'), what to do when connected is false ('use setup_payments to supply the keys'), how to repair a broken webhook, and which sibling to use for plans/prices ('For the plans and prices themselves use list_plans'). When, when-not, and alternatives are all covered.

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