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

Annotations already declare readOnly, idempotent, non-destructive and closed-world, so the safety profile is covered. The description adds genuine behavioral value by disclosing the payload contents ('event types and delivery health') and that the event catalog can include example bodies. It stops short of mentioning pagination or ordering, which for a list tool would be the remaining useful detail.

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?

A single front-loaded sentence that delivers scope, return contents, and the optional catalog behavior with no filler. The trailing 'Free' is short and carries a real cost signal.

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 simple, fully-annotated, zero-required-parameter read tool with no output schema, the description tells the agent what comes back in enough detail to decide to call it. Only minor gaps remain (result ordering/pagination, whether delivery health is computed live).

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 coverage is 100% and the single parameter's own description ('Also return the event catalog with example bodies') is already precise. The description's phrase 'when asked' restates that flag but adds nothing new about format or cost of enabling it. Baseline 3 applies when the schema does the heavy lifting.

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 ('Lists') and resource ('outbound webhooks') and names what is returned: event types, delivery health, and an optional event catalog. The read/list nature is distinguishable from the only sibling webhook tool, dealmachine_webhook_create, though the description never explicitly names an alternative.

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?

Usage is only implied: 'plus the catalog of event types when asked' hints at the include_events flag, and 'Free' signals there is no cost barrier to calling it. There is no statement of when to prefer this over other listing tools or any exclusion/precondition.

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