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

Annotations already cover destructive=true and idempotent=true, so the bar is lower, yet the description still adds real context: what is lost (every night of the route), that the loss is irreversible, that nights cannot be rebuilt by editing, and that deletion must be confirmed with the account holder. This goes well beyond the annotation set.

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 correctly with the destructive action first and the alternative second, but the clause 'the nights cannot be rebuilt by editing' is repeated verbatim in consecutive sentences, which is dead weight in an otherwise tight description.

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?

An output schema exists so return values need no explanation, and annotations carry the safety profile. For this complexity level the description covers purpose, irreversibility, the sibling alternative, and the confirmation prerequisite — nothing an agent needs 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%, so the schema already carries parameter meaning — including the cross-checked `route` label and its refusal behavior. The description adds no syntax or format detail for either parameter, 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 — 'Permanently remove a route and stop watching every night of it' — with the permanence qualifier that separates it from the pause/resume siblings. An agent can distinguish it from pause_itinerary without opening any 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 routes the agent: 'PREFER pause_itinerary when the user may want it back', gives the reason (reversibility), and adds a confirmation protocol ('Ask the account holder which routes they mean before deleting any you did not just create'). When-to-use, when-to-use-something-else, and a prerequisite are all present.

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