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

Annotations already carry destructiveHint=true and idempotentHint=true, so 'Permanently delete' only reinforces what's declared. The added value is the auth requirement ('Requires planner:write'), which is not expressible in the annotations and tells the agent a write scope is needed before invoking.

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?

Two sentences, zero filler, with the permission prerequisite front-loaded. Every sentence earns its place and nothing is buried.

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 the annotations cover reversibility/idempotency. The description adds the scope requirement, leaving only the parameter's origin/semantics unaddressed.

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?

One parameter with 0% schema description coverage; the description never mentions itineraryId, its length bounds, or where an agent would obtain it. The name is largely self-explanatory, so this is a minor but real gap.

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 ('Permanently delete'), resource ('one itinerary'), and scope ('from the connected member account'). An agent can immediately distinguish it from the sibling save_itinerary and remove_saved_guide_item without opening a 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?

The description discloses the required scope ('Requires planner:write'), which is a genuine prerequisite, but gives no when-to-use/when-not guidance or explicit alternative for removing itineraries versus saved guide items. Usage is implied rather than directed.

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