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

Annotations only declare destructive/idempotent flags; the description goes further by explaining exactly what is destroyed (the previous secret becomes invalid), that the new secret is returned one-time only and must be saved immediately, and how to recover from a lost response by replaying the identical body and key. That is precisely the extra context the annotation bar asks for.

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 ordered by importance: what it does, what it requires, how to handle the result and retries. Every clause carries actionable information with no filler.

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?

With no output schema, the description carries the burden of explaining the return value, and it does so explicitly (one-time secret to be saved and propagated to the receiving service). Permission requirements and failure/retry behavior are also covered, leaving nothing an agent needs to call it correctly unstated.

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 all three parameters are already documented, including the idempotencyKey retry rule. The description restates the retry-with-identical-key behavior, adding slight reinforcement but no syntax or meaning the schema lacks, 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?

"Replace the Workspace webhook's signing secret, invalidating the previous secret" gives a specific verb (replace) and a narrowly scoped resource (webhook signing secret), which separates it from siblings like company_update_webhook, company_create_webhook, and company_delete_webhook without needing to name them.

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?

Adds real gating context: "Requires settings permission and explicit intent," telling the agent both the permission prerequisite and that this shouldn't be fired casually. It stops short of naming alternatives (e.g., update_webhook for non-secret changes) or stating when-not-to-use, so it lands just under the top mark.

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