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

Annotations already declare readOnlyHint=true, and the description adds a meaningful behavioral detail beyond that: the tool will ask the user to sign in to Awning if they are not authenticated. This is useful interactive context that the annotations do not provide.

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 short sentences with no filler. The core purpose is front-loaded, and the authentication note in the second sentence earns its place as a prerequisite.

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 read-only list tool with one optional enum parameter, the description covers the essential scope and auth behavior. It does not describe return values or the exact effect of 'period', but the schema's enum values mitigate that gap for a low-complexity 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?

There is one parameter, 'period', with an enum of 'upcoming', 'past', and 'all' but no schema description. The description never mentions the parameter or explains how it filters results, so the agent must infer its meaning entirely from the parameter name and enum values rather than from any tool-level guidance.

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?

The description states the resource ('the signed-in user's bookings') and scope ('across all businesses'), making it clear this is a customer-facing list tool rather than an owner or single-booking tool. It uses an implied verb rather than an explicit one like 'lists', but the meaning is unambiguous.

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 conveys when to use it: when the signed-in user's bookings across all businesses are needed, and it notes an authentication prerequisite. It does not explicitly name alternatives or state when-not-to-use scenarios, leaving some routing decisions to inference.

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