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

Annotations already declare destructiveHint=true and idempotentHint=true, so the bar is lower. The description does add real value beyond them: 'event delivery to it stops immediately' tells the agent the concrete side effect and its timing. However, it says nothing about whether delivery history/logs are retained (relevant given the `list_webhook_deliveries` siblings) or whether the deletion is recoverable.

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 short clauses, front-loaded with the DESTRUCTIVE marker and the action, then the consequence, then the safety instruction. No wasted wording; only minor loss is that the warning prefix duplicates destructiveHint from annotations.

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 only two parameters, full schema coverage, and rich annotations, the description covers what an agent needs to call it safely: the action, the immediate consequence, and the confirmation requirement. The one real gap is disambiguation from the parallel `desk_delete_webhook` tool.

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 `webhook_id` property already documents itself as 'webhook subscription UUID to delete'. The description adds no further semantics about the identifier (e.g., how to obtain it via `list_webhooks`), so 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: 'delete a webhook subscription'. Clear on its own, but there is a sibling `desk_delete_webhook` in the tool list that performs an apparently similar action, and the description does nothing to distinguish the two (nor from `update_webhook`/`create_webhook`).

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?

Gives one explicit procedural rule ('Confirm with the user first'), which is genuine when-to-use guidance for a destructive action. It does not say when to prefer this over `desk_delete_webhook`, or mention alternatives such as disabling delivery via `update_webhook` instead of deleting.

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