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

Annotations already declare destructiveHint=true, openWorldHint=true and idempotentHint=false, so the risk profile is known. The description adds two genuinely useful facts beyond that: the new signing secret is routed to a trusted local helper rather than the tool response, and a local CLI command is returned when a secret is involved. However it stays silent on whether disable is reversible and how updates treat the required url/event_types fields.

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?

Three tight sentences with the operation list front-loaded and no filler; the secret-handling caveat comes before the return-value note, which is the right ordering for an agent skimming.

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 destructive upsert with 9 parameters and no output schema, the description covers modes, secret delivery and the CLI-command return. It omits the upsert resolution rule and whether required fields like event_types are replaced wholesale on update — a meaningful gap for an agent deciding how to call it.

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 only 44% across 9 parameters, so the description should carry weight here — but it only implicitly maps the 'rotate' and 'disable' verbs onto the rotate_secret and disable booleans. Nothing clarifies webhook vs company vs environment scoping, event_types replacement semantics, or the expected_version/idempotency_key retry contract.

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?

Names a specific verb set (create, update, rotate, disable) bound to a concrete resource (signed webhook endpoint), plus a note on secret delivery and return value. What it does is unambiguous, but it never explicitly positions itself against summer_webhooks_list or summer_webhooks_replay, so distinction is left to the sibling names.

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?

Lists the four modes the tool can perform but gives no guidance on which mode applies when, no prerequisites (auth, company vs environment scoping), and no exclusions. The critical selection rule — that create vs update hinges on expected_version being 0 — is only visible in the schema, not the description.

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